Updated on 2024/04/25

写真a

 
UEDA Daijiro
 
Organization
Academic Assembly Institute of Science and Technology NOUGAKU KEIRETSU Assistant Professor
Faculty of Agriculture Department of Agriculture Assistant Professor
Title
Assistant Professor
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Degree

  • 博士(農学) ( 2018.3   新潟大学 )

Research Interests

  • テルぺノイド

  • テルペン

  • 香料

  • 生合成

  • 天然物

  • イソプレノイド

Research Areas

  • Life Science / Bioorganic chemistry  / 生合成

Research History (researchmap)

  • Niigata University   Assistant Professor

    2019.1

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  • Chiba University   Faculty of Engineering, Department of Applied Chemistry and Biotechnology

    2018.4 - 2018.12

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  • Niigata University

    2015.4 - 2018.3

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  • Niigata University

    2013.4 - 2018.3

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Research History

  • Niigata University   Faculty of Agriculture Department of Agriculture   Assistant Professor

    2019.1

Education

  • Niigata University   自然科学研究科博士後期課程   生命・食料科学専攻

    2015.4 - 2018.3

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  • Niigata University   自然科学研究科博士前期課程   生命・食料科学専攻

    2013.4 - 2015.3

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  • Niigata University   Faculty of Agriculture   Department of Applied Biological Chemistry

    2009.4 - 2013.3

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Professional Memberships

  • JAPAN SOCIETY FOR BIOSCIENCE, BIOTECHNOLOGY, AND AGROCHEMISTRY

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  • 日本セトロジー研究会

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Papers

  • Analysis of vitamin D receptor binding affinities of enzymatically synthesized triterpenes including ambrein and unnatural onoceroids

    Daijiro Ueda, Natsu Matsuda, Yuka Takaba, Nami Hirai, Mao Inoue, Taichi Kameya, Tohru Abe, Nao Tagaya, Yasuhiro Isogai, Yoshito Kakihara, Florian Bartels, Mathias Christmann, Tetsuro Shinada, Kaori Yasuda, Tsutomu Sato

    Scientific Reports   14 ( 1 )   2024.1

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    Publishing type:Research paper (scientific journal)   Publisher:Springer Science and Business Media LLC  

    Abstract

    Onoceroids are a rare family of triterpenes. One representative onoceroid is ambrein, which is the main component of ambergris used as a traditional medicine. We have previously identified the onoceroid synthase, BmeTC, in Bacillus megaterium and succeeded in creating ambrein synthase by introducing mutations into BmeTC. Owing to the structural similarity of ambrein to vitamin D, a molecule with diverse biological activities, we hypothesized that some of the activities of ambergris may be induced by the binding of ambrein to the vitamin D receptor (VDR). We demonstrated the VDR binding ability of ambrein. By comparing the structure–activity relationships of triterpenes with both the VDR affinity and osteoclastic differentiation-promoting activity, we observed that the activity of ambrein was not induced via the VDR. Therefore, some of the activities of ambergris, but not all, can be attributed to its VDR interaction. Additionally, six unnatural onoceroids were synthesized using the BmeTC reactions, and these compounds exhibited higher VDR affinity than that of ambrein. Enzymatic syntheses of onoceroid libraries will be valuable in creating a variety of bioactive compounds beyond ambergris.

    DOI: 10.1038/s41598-024-52013-7

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    Other Link: https://www.nature.com/articles/s41598-024-52013-7

  • Synthesis of Drimane-8α,11-diol Using Terpene Cyclase from <i>Bacillus Megaterium</i>

    Keita Ozawa, Yuki Yamamoto, Eigo Fukuda, Seiya Endo, Atsushi Nakayama, Yoko Yasuno, Daijiro Ueda, Tsutomu Sato, Tetsuro Shinada

    Chemistry Letters   52 ( 6 )   520 - 523   2023.6

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    Publishing type:Research paper (scientific journal)   Publisher:The Chemical Society of Japan  

    DOI: 10.1246/cl.230151

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  • Insight into the mechanism of geranyl-β-phellandrene formation catalyzed by Class IB terpene synthases. Reviewed International journal

    Shogo Iwakata, Kazuya Asada, Tomoyuki Nishi, Rafaella Stepanova, So Shinoda, Daijiro Ueda, Masahiro Fujihashi, Yoko Yasuno, Tetsuro Shinada, Tsutomu Sato

    Bioscience, biotechnology, and biochemistry   86 ( 6 )   724 - 729   2022.5

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    Terpene synthase (TS) from Bacillus alcalophilus (BalTS) is the only Class IB TS for which a 3D structure has been elucidated. Recently, geranyl-β-phellandrene, a novel cyclic diterpene, was identified as a product of BalTS in addition to the acyclic β-springene. In the present study, we have provided insight into the mechanism of geranyl-β-phellandrene formation. Deuterium labeling experiments revealed that the compound is produced via a 1,3-hydride shift. In addition, nonenzymatic reactions using divalent metal ions were performed. The enzyme is essential for the geranyl-β-phellandrene formation. Furthermore, BalTS variants targeting tyrosine residues enhanced the yield of geranyl-β-phellandrene and the proportion of the compound of the total products. It was suggested that the expansion of the active site space may allow the conformation of the intermediates necessary for cyclization. The present study describes the first Class IB TSs to successfully alter product profiles while retaining high enzyme activity.

    DOI: 10.1093/bbb/zbac036

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  • Identification and functional analysis of a new type of <i>Z,E</i> ‐mixed prenyl reductase from mycobacteria Reviewed

    Tohru Abe, Mariko Hakamata, Akihito Nishiyama, Yoshitaka Tateishi, Sohkichi Matsumoto, Hisashi Hemmi, Daijiro Ueda, Tsutomu Sato

    The FEBS Journal   289 ( 16 )   4981 - 4997   2022.3

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Wiley  

    DOI: 10.1111/febs.16412

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    Other Link: https://onlinelibrary.wiley.com/doi/full-xml/10.1111/febs.16412

  • Construction of an artificial system for ambrein biosynthesis and investigation of some biological activities of ambrein Reviewed International journal

    Yota Yamabe, Yukina Kawagoe, Kotone Okuno, Mao Inoue, Kanako Chikaoka, Daijiro Ueda, Yuko Tajima, Tadasu K. Yamada, Yoshito Kakihara, Takashi Hara, Tsutomu Sato

    Scientific Reports   10 ( 1 )   19643 - 19643   2020.12

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Springer Science and Business Media LLC  

    <title>Abstract</title>Ambergris, a sperm whale metabolite, has long been used as a fragrance and traditional medication, but it is now rarely available. The odor components of ambergris result from the photooxidative degradation of the major component, ambrein. The pharmacological activities of ambergris have also been attributed to ambrein. However, efficient production of ambrein and odor compounds has not been achieved. Here, we constructed a system for the synthesis of ambrein and odor components. First, we created a new triterpene synthase, “ambrein synthase,” for mass production of ambrein by redesigning a bacterial enzyme. The ambrein yields were approximately 20 times greater than those reported previously. Next, an efficient photooxidative conversion system from ambrein to a range of volatiles of ambergris was established. The yield of volatiles was 8–15%. Finally, two biological activities, promotion of osteoclast differentiation and prevention of amyloid β-induced apoptosis, were discovered using the synthesized ambrein.

    DOI: 10.1038/s41598-020-76624-y

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    Other Link: http://www.nature.com/articles/s41598-020-76624-y

  • Characterization of Class IB Terpene Synthase: The First Crystal Structure Bound with a Substrate Surrogate. Reviewed International journal

    Rafaella Stepanova, Hayato Inagi, Kei Sugawara, Kazuya Asada, Tomoyuki Nishi, Daijiro Ueda, Yoko Yasuno, Tetsuro Shinada, Kunio Miki, Masahiro Fujihashi, Tsutomu Sato

    ACS chemical biology   15 ( 6 )   1517 - 1525   2020.6

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    Terpene synthases (TS) are classified into two broad types, Class I and II, based on the chemical strategy for initial carbocation formation and motif sequences of the catalytic site. We have recently identified a new class of enzymes, Class IB, showing the acceptability of long (C20-C35) prenyl-diphosphates as substrates and no amino acid sequence homology with known TS. Conversion of long prenyl-diphosphates such as heptaprenyl-diphosphate (C35) is unusual and has never been reported for Class I and II enzymes. Therefore, the characterization of Class IB enzymes is crucial to understand the reaction mechanism of the extensive terpene synthesis. Here, we report the crystal structure bound with a substrate surrogate and biochemical analysis of a Class IB TS, using the enzyme from Bacillus alcalophilus (BalTS). The structure analysis revealed that the diphosphate part of the substrate is located around the two characteristic Asp-rich motifs, and the hydrophobic tail is accommodated in a unique hydrophobic long tunnel, where the C35 prenyl-diphosphate, the longest substrate of BalTS, can be accepted. Biochemical analyses of BalTS showed that the enzymatic property, such as Mg2+ dependency, is similar to those of Class I enzymes. In addition, a new cyclic terpene was identified from BalTS reaction products. Mutational analysis revealed that five of the six Asp residues in the Asp-rich motifs and two His residues are essential for the formation of the cyclic skeleton. These results provided a clue to consider the application of the unusual large terpene synthesis by Class IB enzymes.

    DOI: 10.1021/acschembio.0c00145

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  • Insight into Isoprenoid Biosynthesis by Functional Analysis of Isoprenyl Diphosphate Synthases from Mycobacterium vanbaalenii and Mycobacterium tuberculosis. Reviewed International journal

    Tohru Abe, Sadamu Ozaki, Daijiro Ueda, Tsutomu Sato

    Chembiochem : a European journal of chemical biology   2020.6

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    Comprehensive functional analyses of E-isoprenyl diphosphate synthases (E-IDSs) from nonpathogenic Mycobacterium vanbaalenii have been performed. Mv0992 and Mv1577 represent a nonaprenyl diphosphate (E-C45 ) synthase and a geranylgeranyl diphosphate (E-C20 ) synthase, respectively. Although Mv3536 was identified as an E-C20 synthase using a single enzyme, co-incubation of Mv3536 and Z-IDSs (Mv4662 and Mv3822) strongly suggested it releases an intermediate geranyl diphosphate (E-C10 ) during a continuous condensation reaction. Mv0992 and Mv3536 functions differed from those of the previously reported pathogenic Mycobacterium tuberculosis homologues Rv0562 and Rv2173, respectively. Re-analysis of Rv0562 and Rv2173 demonstrated that their functions were similar to those of Mv0992 and Mv3536 (Rv0562: E-C45 synthase; Rv2173: E-C10-15 synthase). The newly proposed functions of Rv0562 and Rv2173 would be in the biosynthesis of menaquinone and glycosyl carrier lipids essential for growth. Furthermore, a reduced allylic diphosphate could be used as the Z-IDS of the Mv3822 substrate, thereby introducing a potentially novel pathway of cyclic sesquarterpene biosynthesis.

    DOI: 10.1002/cbic.202000235

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  • An Aromatic Farnesyltransferase Functions in Biosynthesis of the Anti-HIV Meroterpenoid Daurichromenic Acid. Reviewed International journal

    Haruna Saeki, Ryota Hara, Hironobu Takahashi, Miu Iijima, Ryosuke Munakata, Hiromichi Kenmoku, Kazuma Fuku, Ai Sekihara, Yoko Yasuno, Tetsuro Shinada, Daijiro Ueda, Tomoyuki Nishi, Tsutomu Sato, Yoshinori Asakawa, Fumiya Kurosaki, Kazufumi Yazaki, Futoshi Taura

    Plant physiology   178 ( 2 )   535 - 551   2018.10

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    Language:English   Publishing type:Research paper (scientific journal)  

    Rhododendron dauricum produces daurichromenic acid, an anti-HIV meroterpenoid, via oxidative cyclization of the farnesyl group of grifolic acid. The prenyltransferase (PT) that synthesizes grifolic acid is a farnesyltransferase in plant specialized metabolism. In this study, we demonstrated that the isoprenoid moiety of grifolic acid is derived from the 2-C-methyl-d-erythritol-4-phosphate pathway that takes place in plastids. We explored candidate sequences of plastid-localized PT homologs and identified a cDNA for this PT, RdPT1, which shares moderate sequence similarity with known aromatic PTs. RdPT1 is expressed exclusively in the glandular scales, where daurichromenic acid accumulates. In addition, the gene product was targeted to plastids in plant cells. The recombinant RdPT1 regiospecifically synthesized grifolic acid from orsellinic acid and farnesyl diphosphate, demonstrating that RdPT1 is the farnesyltransferase involved in daurichromenic acid biosynthesis. This enzyme strictly preferred orsellinic acid as a prenyl acceptor, whereas it had a relaxed specificity for prenyl donor structures, also accepting geranyl and geranylgeranyl diphosphates with modest efficiency to synthesize prenyl chain analogs of grifolic acid. Such a broad specificity is a unique catalytic feature of RdPT1 that is not shared among secondary metabolic aromatic PTs in plants. We discuss the unusual substrate preference of RdPT1 using a molecular modeling approach. The biochemical properties as well as the localization of RdPT1 suggest that this enzyme produces meroterpenoids in glandular scales cooperatively with previously identified daurichromenic acid synthase, probably for chemical defense on the surface of R. dauricum plants.

    DOI: 10.1104/pp.18.00655

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  • A Non-Enzymatic Pathway with Superoxide in Intracellular Terpenoid Synthesis. Reviewed International journal

    Daijiro Ueda, Saori Matsugane, Wataru Okamoto, Masayuki Hashimoto, Tsutomu Sato

    Angewandte Chemie (International ed. in English)   57 ( 32 )   10347 - 10351   2018.8

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    Non-C5 -units terpenoids (norisoprenoids) with an acetonyl group are widely distributed in nature. However, studies on the biosynthesis of norisoprenoids are scarce. Now, the C33 norisoprenoid, (all-E)-farnesylfarnesylacetone, was identified from Bacillus spp. and it was elucidated for the first time that superoxide mediates the cleavage of menaquinones (vitamin K) to form norisoprenoids in saponification treatment. From in vivo experiments using gene-disrupted Bacillus subtilis strains targeted for enzymes responsible for menaquinone biosynthesis and for superoxide dismutase, it was suggested that the non-enzymatic cleavage (autoxidation) of menaquinone with superoxide resulted in norisoprenoid synthesis in Bacillus cells. Furthermore, the bioactive norisoprenoids, farnesylacetone and phytone, were produced in Bacillus cells by this novel synthesis system.

    DOI: 10.1002/anie.201805383

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  • Crystal structure and functional analysis of large-terpene synthases belonging to a newly found subclass Reviewed

    Masahiro Fujihashi, Tsutomu Sato, Yuma Tanaka, Daisuke Yamamoto, Tomoyuki Nishi, Daijiro Ueda, Mizuki Murakami, Yoko Yasuno, Ai Sekihara, Kazuma Fuku, Tetsuro Shinada, Kunio Miki

    Chemical Science   9 ( 15 )   3754 - 3758   2018

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Royal Society of Chemistry  

    Thousands of terpenes have been identified to date. However, only two classes of enzymes are known to be involved in their biosynthesis, and each class has characteristic amino-acid motifs. We recently identified a novel large-terpene (C25/C30/C35) synthase, which shares no motifs with known enzymes. To elucidate the molecular mechanism of this enzyme, we determined the crystal structure of a large-β-prene synthase from B. alcalophilus (BalTS). Surprisingly, the overall structure of BalTS is similar to that of the α-domain of class I terpene synthases although their primary structures are totally different from each other. Two novel aspartate-rich motifs, DYLDNLxD and DY(F,L,W)IDxxED, are identified, and mutations of any one of the aspartates eliminate its enzymatic activity. The present work leads us to propose a new subclass of terpene synthases, class IB, which is probably responsible for large-terpene biosynthesis.

    DOI: 10.1039/c8sc00289d

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  • Bioinspired synthesis of pentacyclic onocerane triterpenoids Reviewed

    Florian Bartels, Young J. Hong, Daijiro Ueda, Manuela Weber, Tsutomu Sato, Dean J. Tantillo, Mathias Christmann

    CHEMICAL SCIENCE   8 ( 12 )   8285 - 8290   2017.12

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:ROYAL SOC CHEMISTRY  

    The first chemical synthesis of pentacyclic onocerane triterpenoids has been achieved. A putative biomimetic tricyclization cascade is employed to forge a fused decalin-/oxepane ring system. The synthetic route proceeds to (+)-cupacinoxepin in seven steps and to (+)-onoceranoxide in eight steps in the longest linear sequence, when starting from geranyl chloride and (+)-sclareolide. The bioinspired epoxypolyene cyclization is supported by computational and enzymatic studies.

    DOI: 10.1039/c7sc03903d

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  • Analysis of the Catalytic Mechanism of Bifunctional Triterpene/Sesquarterpene Cyclase: Tyr167 Functions To Terminate Cyclization of Squalene at the Bicyclic Step Reviewed

    Liudmila Tenkovskaia, Mizuki Murakami, Kotone Okuno, Daijiro Ueda, Tsutomu Sato

    CHEMBIOCHEM   18 ( 19 )   1910 - 1913   2017.10

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:WILEY-V C H VERLAG GMBH  

    Onoceroids are a group of triterpenes biosynthesized from squalene or dioxidosqualene by cyclization from both termini. We previously identified a bifunctional triterpene/sesquarterpene cyclase (TC) that constructs a tetracyclic scaffold from tetraprenyl--curcumene (C-35) but a bicyclic scaffold from squalene (C-30) in the first reaction. TC also accepts the bicyclic intermediate as a substrate and generates tetracyclic and pentacyclic onoceroids in the second reaction. In this study, we analyzed the catalytic mechanism of an onoceroid synthase by using mutated enzymes. TCY167A produced an unnatural tricyclic triterpenol, but TCY167L, TCY167F, and TCY167W formed small quantities of tricyclic compounds, which suggested that the bulk size at Y167 contributed to termination of the cyclization of squalene at the bicyclic step. Our findings provide insight into the unique catalytic mechanism of TC, which triggers different cyclization modes depending on the substrate. These findings may facilitate the large-scale production of an onoceroid for which natural sources are limited.

    DOI: 10.1002/cbic.201700329

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  • Biosynthesis of Sesterterpenes, Head-to-Tail Triterpenes, and Sesquarterpenes in Bacillus clausii: Identification of Multifunctional Enzymes and Analysis of Isoprenoid Metabolites Reviewed

    Daijiro Ueda, Hiroaki Yamaga, Mizuki Murakami, Yusuke Totsuka, Tetsuro Shinada, Tsutomu Sato

    CHEMBIOCHEM   16 ( 9 )   1371 - 1377   2015.6

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:WILEY-V C H VERLAG GMBH  

    We performed functional analysis of recombinant enzymes and analysis of isoprenoid metabolites in Bacillus clausii to gain insights into the biosynthesis of rare terpenoid groups of sesterterpenes, head-to-tail triterpenes, and sesquarterpenes. We have identified an (all-E)-isoprenyl diphosphate synthase (E-IDS) homologue as a trifunctional geranylfarnesyl diphosphate (GFPP)/hexaprenyl diphosphate (HexPP)/heptaprenyl diphosphate (HepPP) synthase. In addition, we have redefined the function of a tetraprenyl--curcumene synthase homologue as that of a trifunctional sesterterpene/triterpene/sesquarterpene synthase. This study has revealed that GFPP, HexPP, and HepPP, intermediates of two isoprenoid pathways (acyclic terpenes and menaquinones), are biosynthesized by one trifunctional E-IDS. In addition, GFPP/HexPP and HepPP are the primary substrates for the biosynthesis of acyclic terpenes and menaquinone-7, respectively.

    DOI: 10.1002/cbic.201500138

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  • Cyclization of Squalene from Both Termini: Identification of an Onoceroid Synthase and Enzymatic Synthesis of Ambrein Reviewed

    Daijiro Ueda, Tsutomu Hoshino, Tsutomu Sato

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   135 ( 49 )   18335 - 18338   2013.12

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:AMER CHEMICAL SOC  

    The onoceroids are triterpenoids biosynthesized from squalene or (3S)-2,3-oxidosqualene by cyclization from both termini. We recently revealed that tetraprenyl-beta-curcumene cyclase from Bacillus megaterium (BmeTC) is a bifunctional triterpene/sesquarterpene cyclase that converts head-to-tail tetraprenyl-beta-curcumene and tail-to-tail squalene into pentacyclic and bicyclic products, respectively, in vivo. Here, we reveal that BmeTC has an unprecedented catalytic function in cyclizing squalene from both termini and is the first onoceroid synthase. We also report the first onoceroids from bacterial origin. Our discoveries suggest that symmetric and asymmetric onoceroids could be biosynthesized by a single enzyme via an intermediate cyclized at one terminus of squalene. Furthermore, the new function of BmeTC enabled the synthesis of (+)-ambrein, a major constituent of ambergris that is difficult to obtain naturally, via a mutated squalene-hopene cyclase-catalyzed reaction from easily available squalene.

    DOI: 10.1021/ja4107226

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MISC

  • 龍涎香の主成分アンブレインの人口生合成経路の創出 Invited Reviewed

    上田大次郎, 佐藤努

    バイオサイエンスとインダストリー   79 ( 3 )   224 - 225   2021.5

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    Authorship:Lead author   Language:Japanese   Publishing type:Article, review, commentary, editorial, etc. (scientific journal)  

    J-GLOBAL

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  • Development of ambrein synthase and investigation of some biological activities of ambrein. Invited Reviewed

    上田大次郎, 佐藤努

    Aroma Research   22 ( 2 )   13 - 19   2021.5

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    Authorship:Lead author   Language:Japanese   Publishing type:Article, review, commentary, editorial, etc. (trade magazine, newspaper, online media)  

    J-GLOBAL

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  • 海棲哺乳類大全 彼らの体と生き方に迫る Invited Reviewed

    青木 かがり, 天野 雅男, 石川 創, 磯野 岳臣, 市川 光太郎, 上田 大次郎, 岡崎 雅子, 落合 真理, 蔵本 洋介, 黒田 実加, 酒井 麻衣, 佐々木 基樹, 佐藤 努, 澤 修作, 塩崎 彬, 進藤 順治, 鈴木 一平, 鈴木 美和, 須藤 健二, 関口 雄祐, 田島 木綿子, 塚田 仁次, 坪田 敏男, 徳武 浩司, 中郡 翔太朗, 西田 伸, 服部 薫, 藤原 克則, 堀本 高矩, 松田 純佳, 水口 大輔, 三谷 曜子, 森 健人, 森坂 匡通, 山田 格, 若井 嘉人

    2021.3

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    Language:Japanese   Publishing type:Article, review, commentary, editorial, etc. (trade magazine, newspaper, online media)  

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  • Studies on terpene biosynthetic enzymes and their application to amblein Invited

    Ueda Daijiro

    The TAKASAGO times   183   29 - 32   2019.5

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  • 気になった論文 Invited

    上田 大次郎

    生命科学研究レター   57   21 - 23   2018.10

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  • Study on Ambergris Invited

    上田 大次郎, 佐藤 努

    香料   ( 273 )   53 - 59   2017

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    Language:Japanese   Publisher:日本香料協会  

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  • Enzymatic synthesis of major constituent of ambergris, ambrein Invited

    Ueda Daijiro

    Aroma Res   16 ( 2 )   142 - 143   2015.5

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  • 龍涎香の主成分アンブレインの酵素合成 Invited

    上田 大次郎, 星野力, 佐藤努

    バイオサイエンスとインダストリー   72 ( 5 )   410 - 411   2014.9

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  • 抗酸菌の新しいタイプのZ、E混成型プレニル基還元酵素の同定と機能解析(Identification and functional analysis of a new type of Z,E-mixed prenyl reductase from mycobacteria)

    阿部 透, 袴田 真理子, 西山 晃史, 立石 善隆, 松本 壮吉, 邊見 久, 上田 大次郎, 佐藤 努

    日本細菌学雑誌   77 ( 1 )   68 - 68   2022.2

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    Language:English   Publisher:日本細菌学会  

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  • 抗酸菌由来E型イソプレニル二リン酸合成酵素群の機能解析

    阿部透, 上田大次郎, 佐藤努

    日本放線菌学会大会講演要旨集   35th (CD-ROM)   2021

  • マイコバクテリア由来新規Z,E混成型プレニル基還元酵素の機能解析

    阿部透, 袴田真理子, 西山晃史, 立石善隆, 松本壮吉, 邊見久, 上田大次郎, 佐藤努

    日本放線菌学会大会講演要旨集   35th (CD-ROM)   2021

  • トリテルペン/セスクアテルペン環化酵素の立体構造解析

    亀谷太一, 久保田智巳, 品田哲郎, 上田大次郎, 佐藤努

    イソプレノイド研究会例会講演要旨集   31st (CD-ROM)   2021

  • マイコバクテリア由来新規Z,E混成型プレニル基還元酵素の機能解析によるセスクアテルペン生合成の洞察

    阿部透, 袴田真理子, 西山晃史, 立石善隆, 松本壮吉, 邊見久, 上田大次郎, 佐藤努

    イソプレノイド研究会例会講演要旨集   31st (CD-ROM)   2021

  • Conversion of enzyme-synthesized ambrein to aroma components and pharmacological activity of ambrein

    川越幸奈, 上田大次郎, 柿原嘉人, 原崇, 佐藤努

    日本農芸化学会大会講演要旨集(Web)   2021   2021

  • Analysis of cyclic structure formation mechanism of class IB terpene synthase

    浅田和也, 上田大次郎, 三木邦夫, 藤橋雅宏, 品田哲郎, 佐藤努

    日本農芸化学会大会講演要旨集(Web)   2021   2021

  • 人工龍涎香合成系の構築とアンブレインの新規生物活性の解析

    山辺陽太, 川越幸奈, 上田大次郎, 柿原嘉人, 原崇, 佐藤努

    イソプレノイド研究会例会講演要旨集   30th   2020

  • 抗酸菌由来E型イソプレニル二リン酸合成酵素の機能解析によるイソプレノイド生合成の洞察

    阿部透, 上田大次郎, 佐藤努

    日本農芸化学会関東支部講演要旨集(CD-ROM)   2020   2020

  • ビタミンK生合成機構における「酵素」と「非酵素」による側鎖切断メカニズムの解明

    廣田 佳久, 須原 義智, 佐藤 努, 上田 大次郎

    特別教育・研究報告集   279 - 282   2019

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  • クラスIBテルペン合成酵素の触媒反応の解析

    西智之, STEPANOVA Rafaella, 菅原啓, 上田大次郎, 藤橋雅宏, 三木邦夫, 保野陽子, 品田哲郎, 佐藤努

    日本農芸化学会大会講演要旨集(Web)   2019   2019

  • Mycobacterium属細菌由来新規ヘプタプレニル還元酵素の同定とZ型セスクアテルペン環化酵素の探索

    阿部透, 尾崎真夢, 吉田優里, 三浦彩奈, 相良昌寛, 上田大次郎, 上田大次郎, 金古堅太郎, 三ツ井敏明, 三ツ井敏明, 佐藤努, 佐藤努

    日本放線菌学会大会講演要旨集   34th   2019

  • アンブレインの香気成分への変換および破骨細胞分化誘導活性

    川越幸奈, 上田大次郎, 柿原嘉人, 佐藤努

    イソプレノイド研究会例会講演要旨集   29th   2019

  • Class IB大型テルペン合成酵素の基質認識機構の解析

    藤橋雅宏, 稲木隼人, 西智之, 上田大次郎, 佐藤努, 品田哲朗, 三木邦夫

    イソプレノイド研究会例会講演要旨集   29th   2019

  • Novel and unnatural terpenes found from sesquarterpene cyclase study

    Ueda Daijiro, Yamaga Hiroaki, Okamoto Wataru, Totsuka Yusuke, Shinada Tetsuro, Hoshino Tsutomu, Sato Tsutomu

    Symposium on the Chemistry of Natural Products, symposium papers   56 ( 0 )   2018.7

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    &lt;p&gt;Biosynthetic studies on the sesquarterpenes, a family of C&lt;sub&gt;35 &lt;/sub&gt;terpenes, in Bacillus subtilis have identified a new type of terpene cyclase, tetraprenyl-b-curcumene synthase (TS), which lacks sequence homology to any known terpene synthases. We recently revealed that Bacillus megaterium tetraprenyl-b-curcumene cyclase (TC) is a bifunctional triterpene/sesquarterpene cyclase that converts head-to-tail C&lt;sub&gt;35&lt;/sub&gt; 1 and tail-to-tail C&lt;sub&gt;30&lt;/sub&gt; 3 into pentacyclic 2 and bicyclic 4, respectively, in vivo (Scheme 1). In this presentation, we report novel and unnatural terpenes found from sesquarterpene cyclase (TS and TC) study.&lt;/p&gt;&lt;p&gt;1) We discovered head-to-tail types of novel acyclic sesterterpene 5 and triterpene 6 in B. clausii, and revealed that compounds 5 and 6 are biosynthesized by TS homolog (Bcl-TS) from GFPP and HexPP, respectively (Scheme 2). The present study revealed that TS homologs are a new family of terpene synthases that form not only sesquarterpene but also sesterterpene and triterpene. Genome mining of this new terpene synthase family will lead to discoveries of novel terpene synthases and terpenoids in the future.&lt;/p&gt;&lt;p&gt;2) The enzymatic cyclization of head-to-tail acyclic triterpene 6isolated from Bacillus clausii using B. subtilis TC resulted in the formation of two unnatural pentacyclic triterpenes 7and 8 (Scheme 3). It was revealed that B. subtilis TC, which forms tetracyclic terpenoid scaffold from tetraprenyl-β-curcumene in vivo, could be used to construct the 6/6/6/6/6-fused pentacyclic scaffold in vitro, suggesting that the active site cavity of TC has sufficient space to accommodate this unnatural pentacyclic scaffold. &lt;/p&gt;&lt;p&gt;3) We revealed that TC has an unprecedented catalytic function in cyclizing squalene from both termini and is the first onoceroid synthase (Scheme 4). Also, we report the first onoceroids from bacterial origin. Our discoveries suggested that symmetric and asymmetric onoceroids could be biosynthesized by a single enzyme via an intermediate cyclized at one terminus of squalene. Furthermore, the new function of TC enabled the synthesis of (+)-ambrein 11, a major constituent of ambergris that is difficult to obtain naturally, via a mutated squalene-hopene cyclase–catalyzed reaction from easily available squalene (Scheme 5).&lt;/p&gt;

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  • Large‐terpene合成酵素の酵素的諸性質の解析と部位特異的変異

    西智之, 菅原啓, 小川佳央, 高橋宏忠, 上田大次郎, 藤橋雅宏, 三木邦夫, 保野陽子, 品田哲郎, 佐藤努

    日本蛋白質科学会年会プログラム・要旨集   18th   50   2018.5

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  • Large‐terpene合成酵素の結晶構造解析

    藤橋雅宏, 佐藤努, 田中勇真, 山本大輔, 西智之, 上田大次郎, 村上瑞気, 保野陽子, 関原あい, 福和真, 品田哲郎, 三木邦夫

    日本農芸化学会大会講演要旨集(Web)   2018   ROMBUNNO.3A17p01 (WEB ONLY)   2018.3

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  • Large‐terpene合成酵素の酵素的諸性質の解析と部位特異的変異

    菅原啓, 西智之, 小川佳央, 高橋宏忠, 上田大次郎, 藤橋雅宏, 三木邦夫, 保野陽子, 品田哲郎, 佐藤努

    日本農芸化学会大会講演要旨集(Web)   2018   ROMBUNNO.3A17p02 (WEB ONLY)   2018.3

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  • Large-terpene合成酵素の構造と機能

    藤橋雅宏, 佐藤努, 田中勇真, 山本大輔, 西智之, 上田大次郎, 村上瑞気, 保野陽子, 関原あい, 福和真, 品田哲朗, 三木邦夫

    日本蛋白質科学会年会プログラム・要旨集   18th   2018

  • Large-terpene合成酵素の酵素学的諸性質の解析と部位特異的変異

    西智之, 菅原啓, 小川佳央, 高橋宏忠, 上田大次郎, 藤橋雅宏, 三木邦夫, 保野陽子, 品田哲郎, 佐藤努

    香料・テルペンおよび精油化学に関する討論会講演要旨集   62nd   2018

  • Large-terpene合成酵素の構造機能相関

    藤橋雅宏, 佐藤努, 田中勇真, 山本大輔, 西智之, 上田大次郎, 村上瑞気, 保野陽子, 関原あい, 福和真, 品田哲朗, 三木邦夫

    イソプレノイド研究会例会講演要旨集   28th   2018

  • Bacillus属細菌由来テルペノイドのユニークな生合成経路の解析

    上田大次郎, 松ヶ根沙織, 西智之, 菅原啓, 岡本渉, 藤橋雅宏, 三木邦夫, 橋本昌征, 保野陽子, 品田哲郎, 佐藤努

    イソプレノイド研究会例会講演要旨集   28th   2018

  • 3P-269 Biosynthesis of rare terpenoids in Bacillus clausii

    Ueda Daijiro, Yamaga Hiroaki, Murakami Mizuki, Totsuka Yusuke, Shinada Tetsuro, Sato Tsutomu

    日本生物工学会大会講演要旨集   67   338 - 338   2015

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  • セスクアテルペン環化酵素を基軸とするテルペン創出経路の開拓

    上田大次郎, 山鹿宏彰, 岡本渉, 遠塚悠輔, 品田哲郎, 星野力, 佐藤努

    天然有機化合物討論会講演要旨集(Web)   56th ( 0 )   103‐108(J‐STAGE)   2014

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    Language:Japanese   Publisher:Symposium on the Chemistry of Natural Products Steering Committee  

    <p>Biosynthetic studies on the sesquarterpenes, a family of C<sub>35 </sub>terpenes, in Bacillus subtilis have identified a new type of terpene cyclase, tetraprenyl-b-curcumene synthase (TS), which lacks sequence homology to any known terpene synthases. We recently revealed that Bacillus megaterium tetraprenyl-b-curcumene cyclase (TC) is a bifunctional triterpene/sesquarterpene cyclase that converts head-to-tail C<sub>35</sub> 1 and tail-to-tail C<sub>30</sub> 3 into pentacyclic 2 and bicyclic 4, respectively, in vivo (Scheme 1). In this presentation, we report novel and unnatural terpenes found from sesquarterpene cyclase (TS and TC) study.</p><p>1) We discovered head-to-tail types of novel acyclic sesterterpene 5 and triterpene 6 in B. clausii, and revealed that compounds 5 and 6 are biosynthesized by TS homolog (Bcl-TS) from GFPP and HexPP, respectively (Scheme 2). The present study revealed that TS homologs are a new family of terpene synthases that form not only sesquarterpene but also sesterterpene and triterpene. Genome mining of this new terpene synthase family will lead to discoveries of novel terpene synthases and terpenoids in the future.</p><p>2) The enzymatic cyclization of head-to-tail acyclic triterpene 6isolated from Bacillus clausii using B. subtilis TC resulted in the formation of two unnatural pentacyclic triterpenes 7and 8 (Scheme 3). It was revealed that B. subtilis TC, which forms tetracyclic terpenoid scaffold from tetraprenyl-β-curcumene in vivo, could be used to construct the 6/6/6/6/6-fused pentacyclic scaffold in vitro, suggesting that the active site cavity of TC has sufficient space to accommodate this unnatural pentacyclic scaffold. </p><p>3) We revealed that TC has an unprecedented catalytic function in cyclizing squalene from both termini and is the first onoceroid synthase (Scheme 4). Also, we report the first onoceroids from bacterial origin. Our discoveries suggested that symmetric and asymmetric onoceroids could be biosynthesized by a single enzyme via an intermediate cyclized at one terminus of squalene. Furthermore, the new function of TC enabled the synthesis of (+)-ambrein 11, a major constituent of ambergris that is difficult to obtain naturally, via a mutated squalene-hopene cyclase–catalyzed reaction from easily available squalene (Scheme 5).</p>

    DOI: 10.24496/tennenyuki.56.0_Oral18

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  • セスクアテルペン環化酵素の部位特異的変異および非天然型テルペンの創出

    上田大次郎, 岡本渉, 山本彩乃, 遠塚悠輔, 品田哲郎, 仲野千秋, 佐藤努

    香料・テルペンおよび精油化学に関する討論会講演要旨集   57th   369 - 371   2013.10

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Presentations

  • Analysis of the product chain length determination mechanism of bacterial medium-chain Z-isoprenyl diphosphate synthases

    2024.3 

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  • Characterizaion of a novel terpene synthase from insects

    2024.3 

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  • Identification of non-terminal cyclizing tri/sesquarterpene cyclase

    2024.3 

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  • アンブレインと非天然型オノセロイドのビタミンD受容体結合能の解析

    松田夏, 平井奈実, 鷹羽優香, 井上真緒, 亀谷太一, 達谷窟奈緒, 安田佳織, 磯貝泰弘, 柿原嘉人, 品田哲郎, 上田大次郎, 佐藤努

    第67回香料・テルペンおよび精油化学に関する討論会  2023.10 

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  • ドリマン骨格のケモエンザイマティック合成

    品田哲郎, 小澤圭太, 遠藤聖也, 福田瑛吾, 中山淳, 保野陽子, 久保田智巳, 亀谷太一, 上田大次郎, 佐藤努

    第67回香料・テルペンおよび精油化学に関する討論会  2023.10 

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  • 昆虫由来新規テルペン合成酵素の諸性質の解析とゲノムマイニング

    上田大次郎, 平井知愛, 冨士川成美, 佐藤努

    第67回香料・テルペンおよび精油化学に関する討論会  2023.10 

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  • 龍涎香主成分アンブレインの香気成分への変換に関する解析

    木村優太, 天野未結, 三宅康隆, 品田哲郎, 上田大次郎, 佐藤努

    第67回香料・テルペンおよび精油化学に関する討論会  2023.10 

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  • アンブレイン高生産に向けた進化工学系の構築

    上田大次郎, 佐藤諒, 藤井明日香, 大谷悠介, 梅野太輔, 佐藤努

    第75回日本生物工学会大会  2023.9 

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  • 昆虫由来新規テルペン合成酵素の諸性質の解析とゲノムマイニング

    平井知愛, 上田大次郎, 冨士川成美, 佐藤努

    第75回日本生物工学会大会  2023.9 

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  • アンブレイン合成酵素の部位特異的変異による構造安定化・耐熱化

    山澤友葉, 亀谷太一, 久保田智巳, 石川一彦, 上田大次郎, 佐藤努

    第75回日本生物工学会大会  2023.9 

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  • 昆虫由来新型テルペン合成酵素の諸性質の解析

    上田大次郎, 平井知愛, 冨士川成美, 佐藤努

    予知生合成科学 2023若手合宿勉強会  2023.8 

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  • アンブレインのビタミンD受容体結合能と構造活性相関:酵素合成したトリテルペンを用いた解析

    上田 大次郎, 松田, 夏, 平井, 奈実, 鷹羽, 優香, 井上, 真緒, 亀谷, 太一, 三宅, 康隆, 達谷窟, 奈緒, 安田, 佳織, 柿原, 嘉人, 原, 崇, 品田, 哲郎, 佐藤 努

    日本ビタミン学会第75回大会  2023.6 

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  • 新しいタイプの Z,E 混成型プレニル基還元酵素の同定と機能解析

    阿部 透, 若松のぞみ, 西山晃史, 立石善隆, 松本壮吉, 上田大次郎, 佐藤 努

    学術変革領域研究(A)第2回公開シンポジウム  2023.6 

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  • Identification of a new type of enzyme that reduces E- and Z-isoprene units

    2023.3 

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  • Biosynthesis of unnatural triterpenes and vitamin D receptor binding ability of ambrein

    2023.3 

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  • Construction of a Directed Evolution System for the Ambrein Synthase

    2023.3 

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  • Insight into isoprenoids biosynthesis in mycobacteria by identification and functional analysis of isoprenyl diphosphate synthases and a new type of prenyl reductase Invited

    U.S.-Japan Cooperative Medical Sciences Program 2023 International Conference on Emerging Infectious Diseases in the Pacific Rim  2023.3 

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  • ハムシ由来新型テルペン合成酵素の酵素諸性質の解析

    上田大次郎, 冨士川成美, 平井知愛, 佐藤 努

    第 62回 新潟生化学懇話会  2022.7 

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  • 抗酸菌由来 Z型イソプレニル二リン酸合成酵素で新たに見出された鎖長決定因子

    山之内 菜央 , 阿部 透 , 山崎 智也 , 上田 大次郎 , 佐藤 努

    第 62回 新潟生化学懇話会  2022.7 

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  • 抗酸菌由来のZ型プレニル基を還元する新しいタイプの酵素の同定

    阿部透, 若松のぞみ, 西山晃史, 松本壮吉, 上田 大次郎, 佐藤 努

    第 62回 新潟生化学懇話会  2022.7 

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  • マイコバクテリア由来新規Z,E混成型プレニル基還元酵素の機能解析

    阿部 透, 袴田 真理子, 西山 晃史, 立石 善隆, 松本 壮吉, 邊見 久, 上田 大次郎, 佐藤 努

    日本農芸化学会2022年度大会  2022.3 

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  • 二機能性トリテルペン/セスクアテルペン環化酵素におけるセスクアテルペン環化に重要なアミノ酸残基の解析

    船津 莉香, 鷹羽 優香, 品田 哲郎, 亀谷 太一, 久保田 智巳, 上田 大次郎, 佐藤 努

    2022.3 

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  • クラスIBテルペン合成酵素のゲノムマイニング

    大塚 生、藤橋 雅宏、品田 哲郎、上田 大次郎、佐藤 努

    日本農芸化学会2022年度大会  2022.3 

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  • 立体構造に基づくアンブレイン合成酵素の触媒機構解析と構造安定化

    亀谷 太一、久保田 智巳、小山 裕彰、山澤 友葉、上田 大次郎、品田 哲郎、佐藤 努

    日本農芸化学会2022年度大会  2022.3 

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  • ClassIBテルペン合成酵素の基質/マグネシウムイオン結合型立体構造を基にした変異酵素解析

    岩片 奨悟, 金本 壮平, 三木 邦夫, 深井 周也, 藤橋 雅宏, 品田 哲郎, 上田 大次郎, 佐藤 努

    日本農芸化学会2022年度大会  2022.3 

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  • Construction of an artificial system for ambrein biosynthesis and investigation of some biological activities of ambrein

    Yota Yamabe, Yukina Kawagoe, Kotone Okuno, Mao Inoue, Kanako Chikaoka, Daijiro Ueda, Yuko Tajima, Tadasu K. Yamada, Yoshito Kakihara, Takashi Hara, Tsutomu Sato

    PACIFICHEM 2021 INTERNATIONAL CHEMICAL CONGRESS OF PACIFIC BASIN SOCIETIES  2021.12 

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  • Functional analyses of isoprenyl diphoshate synthases from mycobacteria

    Tohru Abe, Sadamu Ozaki, Daijiro Ueda, Tsutomu Sato

    PACIFICHEM 2021 INTERNATIONAL CHEMICAL CONGRESS OF PACIFIC BASIN SOCIETIES  2021.12 

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  • Biosynthesis of isoprenyl diphosphates in mycobacteria

    Tohru Abe, Sadamu Ozaki, Daijiro Ueda, Tsutomu Sato

    7th International Symposium on Strategies for Sustainability in Food Production, Agriculture and the Environment 2021  2021.12 

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  • Construction of an artificial system for ambrein biosynthesis and investigation of some biological activities of ambrein

    Yota Yamabe, Yukina Kawagoe, Kotone Okuno, Mao Inoue, Kanako Chikaoka, Daijiro Ueda, Yuko Tajima, Tadasu K. Yamada, Yoshito Kakihara, Takashi Hara, Tsutomu Sato

    7th International Symposium on Strategies for Sustainability in Food Production, Agriculture and the Environment 2021  2021.12 

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  • 抗酸菌のイソプレノイド生合成に関わる鎖伸長酵素と還元酵素の機能解析

    阿部 透, 袴田真理子, 西山晃史, 立石善隆, 松本壮吉, 邊見 久, 上田大次郎, 佐藤 努

    第5回抗酸菌研究会  2021.11 

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  • Constructioun of an artificial system for ambrein biosynthesis and investigation of some biological activities of ambrein

    2021.10 

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  • トリテルペン/セスクアテルペン環化酵素の立体構造解析

    亀谷太一, 久保田智巳, 品田哲郎, 上田大次郎, 佐藤 努

    第 31 回 イソプレノイド研究会例会  2021.9 

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  • マイコバクテリア由来新規 Z, E 混成型プレニル基還元酵素の機能解析による セスクアテルペン生合成の洞察

    阿部 透, 袴田真理子, 西山晃史, 立石善隆, 松本壮吉, 邊見 久, 上田大次郎, 佐藤 努

    第 31 回 イソプレノイド研究会例会  2021.9 

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  • マイコバクテリア由来新規 Z, E 混成型プレニル基還元酵素の機能解析

    阿部 透, 袴田 真理子, 西山 晃史, 立石 善隆, 松本 壮吉, 邊見 久, 上田 大次郎, 佐藤 努

    第35回(2021年度)日本放線菌学会大会  2021.9 

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  • 抗酸菌由来 E 型イソプレニル二リン酸合成酵素群の機能解析

    阿部 透, 上田 大次郎, 佐藤 努

    第35回(2021年度)日本放線菌学会大会  2021.9 

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  • Constructioun of an artificial system for ambrein biosynthesis and investigation of some biological activities of ambrein

    The 63rd SYMPOSIUM on THE CHEMISTRY OF NATURAL PRODUCTS  2021.9 

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  • Bacillus 属細菌由来新規テルぺノイド生合成の解析と利用 Invited

    上田大次郎

    第61回新潟生化学懇話会  2021.7 

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  • 部位特異的変異による二機能性テルペン環化酵素の触媒機構解析と 新規セスクアテルペンの創出

    鷹羽優香, 上田大次郎, 品田哲郎, 佐藤努

    第61回新潟生化学懇話会  2021.7 

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  • アンブレイン生合成酵素の進化工学

    藤井明日香, 上田大次郎, 大谷悠介, 梅野太輔, 佐藤努

    第61回新潟生化学懇話会  2021.7 

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  • 抗酸菌由来新規Z, E混成型プレニル基還元酵素の機能解析

    阿部透, 袴田真理子, 西山晃史, 立石善隆, 松本壮吉, 邊見久, 上田大次郎, 佐藤努

    第61回新潟生化学懇話会  2021.7 

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  • トリテルペン/セスクアテルペン環化酵素のX 線結晶構造解析

    亀谷太一, 久保田智巳, 品田哲郎, 上田大次郎, 佐藤努

    第61回新潟生化学懇話会  2021.7 

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  • クラスIB テルペン合成酵素のゲノムマイニング

    大塚生, 藤橋雅宏, 品田哲郎, 上田大次郎, 佐藤努

    第61回新潟生化学懇話会  2021.7 

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  • クラスⅠB テルペン合成酵素の反応中に形成される副生成物の解析

    篠田奏, 上田大次郎, 品田哲郎, 佐藤努

    第61回新潟生化学懇話会  2021.7 

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  • Analysis of cyclic structure formation mechanism of class IB terpene synthase

    2021.3 

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  • Conversion of enzyme-synthesized ambrein to aroma components and pharmacological activity of ambrein

    2021.3 

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  • Functional analysis of E-isoprenyl diphosphate synthases from Mycobacterium tuberculosis

    2021.3 

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  • Search for novel sesquarterpenes from Mycobacterium spp.

    Nozomi Wakamatsu, Tohru Abe, Daijiro Ueda, Tsutomu Sato

    KAAB International Symposium 2021  2021.1 

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  • Insight into Isoprenoid Biosynthesis by Functional Analysis of Isoprenyl Diphosphate Synthases from Mycobacterium species

    Tohru Abe, Daijiro Ueda, Tsutomu Sato

    KAAB International Symposium 2021  2021.1 

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  • Construction of artificial ambrein biosynthetic pathway and genome mining of a novel triterpene/sesquarterpene cyclase

    Yuka Sagae, Yota Yamabe, Mao Inoue, Kotone Okuno, Kanako Chikaoka, Daijiro Ueda, Tsutomu Sato

    KAAB International Symposium 2021  2021.1 

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  • The conversion of ambrein to volatile components of ambergris and new biological activities of ambrein

    Yukari Kuboi, Yukina Kawagoe, Daijiro Ueda, Yoshito Kakihara, Takashi Hara, Tsutomu Sato

    KAAB International Symposium 2021  2021.1 

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  • Characterization of Class IB terpene synthase

    Kazuya Asada, Rafaella Stepanova, Kei Sugawara, Tomoyuki Nishi, Daijiro Ueda, Syuto Inagi, Kunio Miki, Masahiro Fujihashi, Yoko Yasuno, Tetsuro Shinada, Tsutomu Sato

    KAAB International Symposium 2021  2021.1 

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  • 抗酸菌由来E型イソプレニル二リン酸合成酵素の機能解析による イソプレノイド生合成の洞察

    阿部 透, 上田 大次郎, 佐藤 努

    日本農芸化学会 関東支部 2020 年度大会  2020.11 

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  • 非末端環化型トリテルペン/セスクアテルペン環化酵素のゲノムマイニング

    寒河江 侑加, 井上 真緒, 上田 大次郎, 佐藤 努

    第64回香料・テルペンおよび精油化学に関する討論会  2020.10 

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  • クラスⅠBテルペン合成酵素の諸性質解析、マイナー生成物の同定および環化に重要な残基の特定

    浅田 和也, Rafaella Stepanova, 菅原 啓, 西 智之, 上田大次郎, 稲木 隼人, 三木 邦夫, 藤橋 雅宏, 保野 陽子, 品田 哲郎, 佐藤 努

    第64回香料・テルペンおよび精油化学に関する討論会  2020.10 

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  • 抗酸菌由来イソプレニル二リン酸合成酵素の機能解析によるイソプレノイド生合成の洞察

    阿部 透, 上田 大次郎, 佐藤 努

    第64回香料・テルペンおよび精油化学に関する討論会  2020.10 

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  • アンブレインから龍涎香の香気成分への変換とアンブレインの新規生物活性

    久保井 友夏梨, 川越 幸奈, 上田 大次郎, 柿原 嘉人, 原 崇, 佐藤 努

    第64回香料・テルペンおよび精油化学に関する討論会  2020.10 

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  • 龍涎香主成分アンブレインの効率的酵素合成法の創出

    山辺 陽太, 上田 大次郎, 佐藤 努

    第64回香料・テルペンおよび精油化学に関する討論会  2020.10 

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  • Mycobacterium moriokaenese由来新規セスクアテルペンの同定

    若松 のぞみ, 阿部 透, 上田 大次郎, 佐藤 努

    第64回香料・テルペンおよび精油化学に関する討論会  2020.10 

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  • 非天然型オノセロイドの酵素合成

    平井 奈実, 井上 真緒, 上田 大次郎, 品田 哲郎, 佐藤 努

    第64回香料・テルペンおよび精油化学に関する討論会  2020.10 

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  • 抗酸菌由来E型イソプレニル二リン酸合成酵素の機能解析によるイソプレノイド生合成の洞察

    阿部 透, 上田 大次郎, 佐藤 努

    第30回イソプレノイド研究会  2020.9 

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  • 人工龍涎香合成系の構築とアンブレインの新規生物活性の解析

    山辺 陽太, 川越 幸奈, 奧野 琴音, 上田 大次郎, 柿原 嘉人, 原 崇, 佐藤 努

    第30回イソプレノイド研究会  2020.9 

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  • 抗酸菌由来イソプレニル二リン酸合成酵素の機能解析によるイソプレノイド生合成の洞察

    阿部 透, 尾崎 真夢, 上田 大次郎, 佐藤 努

    第62回天然有機化合物討論会  2020.9 

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  • 天然有機化合物の生合成研究分野におけるビッグデータ利用 Invited

    佐藤 努, 上田 大次郎

    第23回BDA研究会  2020.5 

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  • Construction of the artificial synthesis pathway of ambergris

    2020.3 

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  • Analysis of isoprenyl diphosphates biosynthesis from Mycobacterium spp.

    2020.3 

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  • Search and use of ambrein/onoceroids-producing bacteria from sperm whale gut

    2020.3 

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  • 抗酸菌由来イソプレニル二リン酸合成酵素の機能解析

    阿部 透, 尾崎真夢, 上田 大次郎, 佐藤 努

    第94回日本細菌学会  2020.3 

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  • Characterization and mutation of class-IB terpene synthase

    Rafaella Stepanova, Tomoyuki Nishi, Kei Sugawara, Kao Ogawa, Hirotada Takahashi, Daijiro Ueda, Masahiro Fujihashi, Kunio Miki, Yoko Yasuno, Tetsuro Shinada, Tsutomu Sato

    3rd International Conference on Natural Products Discovery & Development in the Genomic Era  2020.1 

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  • A Non‐Enzymatic Pathway with Superoxide in Intracellular Terpenoid Synthesis

    Daijiro Ueda, Saori Matsugane, Wataru Okamoto, Masayuki Hashimoto, Tsutomu Sato

    3rd International Conference on Natural Products Discovery & Development in the Genomic Era  2020.1 

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  • 酵素合成されたトリテルペンを⽤いた⽣物活性解析

    上田大次郎, 松田 夏, 平井 奈実, 鷹羽 優香, 井上 真緒, 亀谷太一, 達谷窟奈緒, 安田佳織, 磯貝泰弘, 柿原嘉人, 品田哲郎, 佐藤 努

    第 33回 イソプレノイド研究会例会  2023.9 

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  • ⾮末端環化型トリテルペン/セスクアテルペン環化酵素の同定

    鈴木和佳奈, 寒河江侑加, 井上真緒, 上田大次郎, 品田哲郎, 佐藤 努

    第 33 回 イソプレノイド研究会例会  2023.9 

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  • 細菌の中鎖Z 型イソプレニル⼆リン酸合成酵素の鎖⻑制御機構の解析

    山之内菜央, 阿部 透, 山崎智也, 上田大次郎, 佐藤 努

    第 33 回 イソプレノイド研究会例会  2023.9 

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  • 抗酸菌由来の新規テルペンと新しいタイプのプレニル基還元酵素の同定

    阿部 透, 若松のぞみ, 西山晃史, 立石善隆, 松本壮吉, 上田大次郎, 佐藤 努

    第6回抗酸菌研究会  2022.11 

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  • Class IBテルペン合成酵素の変異解析とゲノムマイニングによる新規テルペンの創出

    岩片奨悟, 大塚 生, 金本壮平, 深井周也, 藤橋雅宏, 品田哲郎, 上田大次郎, 佐藤 努

    第66回香料・テルペンおよび精油化学に関する討論会  2022.11 

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  • Class IBテルペン合成酵素の触媒機構解析

    岩片奨悟, 金本壮平, 深井周也, 藤橋雅宏, 品田哲郎, 上田大次郎, 佐藤 努

    生物工学若手研究者の集い夏のオンラインセミナー2022  2022.10 

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  • Class IBテルペン合成酵素のゲノムマイニングと変異酵素解析

    岩片 奨悟, 大塚 生, 金本 壮平, 深井 周也, 藤橋 雅宏, 品田 哲郎, 上田 大次郎, 佐藤 努

    第 32 回 イソプレノイド研究会例会  2022.9 

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  • E-及びZ-イソプレンユニットを還元する新しいタイプの酵素の同定

    阿部 透, 若松 のぞみ, 西山 晃史, 立石 善隆, 松本 壮吉, 上田 大次郎, 佐藤 努

    第 32 回 イソプレノイド研究会例会  2022.9 

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  • 二機能性トリテルペン/セスクアテルペン環化酵素におけるセスクアテルペン環化に重要なアミノ酸残基の機能解析

    船津 莉香, 鷹羽 優香, 品田 哲郎, 亀谷 太一, 久保田 智巳, 上田 大次郎, 佐藤 努

    第 32 回 イソプレノイド研究会例会  2022.9 

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  • 抗酸菌由来新規Z,E混成プレニル基還元酵素の同定と機能解析

    阿部 透, 袴田真理子, 西山晃史, 立石善隆, 松本壮吉, 邊見 久, 上田大次郎, 佐藤 努

    第64回天然有機化合物討論会  2022.9 

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  • マイコバクテリア由来のZ型プレニル基を還元する新しいタイプの酵素の同定

    阿部 透・若松のぞみ・西山晃史・立石善隆・松本壮吉・上田大次郎・佐藤 努

    学術変革領域研究(A)「予知生合成科学」 第一回若手シンポジウム  2022.8 

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  • Identification and functional analysis of a new type of Z,E-mixed prenyl reductase from mycobacteria

    2022.3 

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  • アンブレインの香気成分への変換および破骨細胞分化誘導活性

    川越幸奈, 上田大次郎, 柿原嘉人, 佐藤努

    日本ハーブ療法研究会第7回学術集会  2019.12 

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  • Mycobacterium属細菌由来新規Z, E-ヘプタプレニル還元酵素の同定

    阿部 透, 尾崎 真夢, 吉田 優里, 三浦 彩奈, 相良 昌寛, 上田 大次郎, 佐藤 努

    第4回抗酸菌研究会  2019.11 

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  • Identification of a novel heptaprenyl reductase and search for a Z-type sesquarterpene cyclase from Mycobacterium spp. International conference

    Tohru Abe, Sadamu Ozaki, Yuri Yoshida, Ayana Miura, Masahiro Sagara, Daijiro Ueda, Kentaro Kaneko, Toshiaki Mitsui, Tsutomu Sato

    KAAB International Symposium 2019  2019.11 

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  • Characterization and mutation of class-IB terpene synthase International conference

    Ueda Daijiro

    KAAB International Symposium 2019  2019.11 

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  • マッコウクジラ由来アンブレイン・オノセロイド生産菌の探索と利用

    近岡花菜子, 川邊 舞, 上田大次郎, 山田 格, 田島木綿子, 佐藤 努

    第29回イソプレノイド研究会例会  2019.10 

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  • アンブレインの人口生合成経路のリデザイン

    山辺陽太, 奥野琴音, 井上真緒, 上田大次郎, 佐藤努

    第29回イソプレノイド研究会例会  2019.10 

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  • Mycobacterium属細菌由来新規Z, E-ヘプタプレニル還元酵素の同定とZ型セスクアテルペン環化酵素の探索

    阿部 透, 尾崎 真夢, 吉田 優里, 三浦 彩奈, 相良 昌寛, 上田 大次郎, 金古 堅太郎, 三ツ井 敏明, 佐藤 努

    第29回イソプレノイド研究会例会  2019.10 

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  • アンブレインの香気成分への変換および破骨細胞分化誘導活性

    川越幸奈, 上田大次郎, 柿原嘉人, 佐藤努

    第29回イソプレノイド研究会例会  2019.10 

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  • Mycobacterium属細菌由来新規ヘプタプレニル還元酵素の同定とZ型セスクアテルペン環化酵素の探索

    阿部 透, 尾崎 真夢, 吉田 優里, 三浦 彩奈, 相良 昌寛, 上田 大次郎, 金古 堅太郎, 三ツ井 敏明, 佐藤 努

    第63回香料・テルペンおよび精油化学に関する討論会  2019.9 

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  • Mycobacterium属細菌由来新規ヘプタプレニル還元酵素の同定とZ型セスクアテルペン環化酵素の探索

    阿部 透, 尾崎 真夢, 吉田 優里, 三浦 彩奈, 相良 昌寛, 上田 大次郎, 金古 堅太郎, 三ツ井 敏明, 佐藤 努

    第34回日本放線菌学会大会  2019.9 

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  • Bacillus 属細菌の新規テルペノイド生合成経路の解析

    上田大次郎, 藤橋雅宏, 松ヶ根沙織, 岡本渉, 西智之, 村上瑞気, 三木邦夫, 保野陽子, 品田哲郎, 橋本昌征, 佐藤努

    第61回天然有機化合物討論会  2019.9 

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  • テルペン生合成における活性酸素による非酵素的経路の解明

    上田大次郎, 松ヶ根沙織, 岡本 渉, 橋本昌征, 佐藤 努

    第60回新潟生化学懇話会  2019.7 

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  • スクアレン‐アンブレイン環化酵素の創出

    山辺陽太, 奥野琴音, 井上真緒, 上田大次郎, 佐藤努

    第60回新潟生化学懇話会  2019.7 

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  • マッコウクジラ由来アンブレイン・オノセロイド生産菌の探索と利用

    近岡花菜子, 川邊 舞, 上田大次郎, 山田 格, 田島木綿子, 佐藤 努

    第60回新潟生化学懇話会  2019.7 

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  • Characterization and site-directed mutagenesis of class-IB terpene synthase

    Rafaella Stepanova, Tomoyuki Nishi, Kei Sugawara, Kao Ogawa, Hirotada Takahashi, Daijiro Ueda, Masahiro Fujihashi, Kunio Miki, Yoko Yasuno, Tetsuro Shinada, Tsutomu Sato

    第60回新潟生化学懇話会  2019.7 

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  • Mycobacterium属細菌由来新規プレニル二リン酸還元酵素の同定と新型セスクアテルペン環化酵素の探索

    阿部 透, 尾崎 真夢, 吉田 優里, 三浦 彩奈, 相良 昌寛, 上田 大次郎, 金古 堅太郎, 三ツ井 敏明, 佐藤 努

    第60回新潟生化学懇話会  2019.7 

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  • Enzymatic synthesis of major constituent of ambergris, ambrein Invited International conference

    Daijiro Ueda

    International Symposium-Workshop 2019 Scientific studies of Marine Mammals in Asia-As seen in Ongoing activities in Japan-  2019.6 

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  • 共用設備を利用したケミカルバイオロジー研究~希少有用天然物の研究~

    上田 大次郎

    文部科学省 先端研究基盤共用促進事業キックオフ・シンポジウム  2019.2 

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  • スクアレン‐アンブレイン環化酵素の創出:アンブレインはスクレンレンから二つの経絡を経由して一つの酵素により合成される

    山辺陽太, 奥野琴音, 井上真緒, 上田大次郎, 佐藤努

    第18回日本蛋白質科学会年会  2018.6 

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  • 非対称オノセロイド生合成経路の特異性の進化デザイン

    上田 大次郎

    第2回新学術領域研究「生合成リデザイン」若手シンポジウム  2018.5 

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  • アセトニル基をもつノルイソプレノイド類の生合成:ビタミンKの非酵素的開裂

    上田 大次郎, 松ヶ根 沙織, 岡本 渉, 橋本 昌征, 佐藤 努

    日本農芸化学会2018年度大会  2018.3 

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  • Creation of squalene-ambrein cyclase: ambrein can be synthesized from squalene by one enzyme through two pathways International conference

    Ueda Daijiro

    KAAB International Symposium 2017  2017.9 

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  • スクアレンーアンブレイン環化酵素の創出:アンブレインはスクアレンから2つの経路を通して1つの酵素によって合成できる

    上田大次郎, 奥野琴音, 星野力, 佐藤努

    第69回日本生物工学会大会  2017.9 

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  • マッコウクジラ由来アンブレイン生産菌の探索

    上田大次郎, 川邊舞, 山田格, 田島木綿子, 佐藤努

    セトロジー研究会  2017.6 

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  • Biosynthesis of Sesterterpenes, Head-to-Tail Triterpenes, and Sesquarterpenes in Bacillus clausii: Identification of Multifunctional Enzymes and Analysis of Isoprenoid Metabolite International conference

    Ueda Daijiro

    2017.3 

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  • アセトニル基をもつノルイソプレノイド類の生合成:ビタミンKの非酵素的開裂

    上田 大次郎, 松ヶ根 沙織, 岡本 渉, 橋本 昌征, 佐藤 努

    日本農芸化学会2017年度大会  2017.3 

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  • ポリプレニルアセトン類の生合成:活性酸素によるメナキノンの非酵素的開裂反応

    上田大次郎, 岡本渉, 橋本昌征, 佐藤努

    第60回香料・テルペンおよび精油化学に関する討論会  2016.10 

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  • ポリプレニルアセトン類の生合成:活性酸素によるメナキノンの非酵素的開裂反応

    上田大次郎, 岡本渉, 橋本昌征, 佐藤努

    日本農芸化学会関東支部2016年度支部大会  2016.10 

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  • Biosynthesis of polyprenylacetone: proposal for non-enzymatic cleavage of menaquinone by reactive oxygen species International conference

    Ueda Daijiro

    KAAB International Symposium 2016  2016.9 

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  • スクアレン‐アンブレイン環化酵素の創出:アンブレインはスクアレンから一つの酵素によって2つの経路を経て合成できる

    奥野琴音, 上田大次郎, 村上瑞気, 星野力, 佐藤努

    第26回イソプレノイド研究会  2016.9 

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  • ポリプレニルアセトン類の生合成:活性酸素によるメナキノンの非酵素的開裂反応

    上田大次郎, 岡本渉, 橋本昌征, 佐藤努

    第26回イソプレノイド研究会  2016.9 

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  • Biosynthesis of polyprenylacetone: proposal for non-enzymatic cleavage of menaquinone by reactive oxygen species

    Ueda Daijiro

    2016.7 

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  • 龍涎香主成分ambreinの酵素合成

    上田大次郎, 星野力, 佐藤努

    セトロジー研究会  2016.6 

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  • スクアレンからアンブレインへの一段階酵素合成

    奥野琴音, 上田大次郎, 星野力, 佐藤努

    日本農芸化学会2016年度大会  2016.3 

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  • Biosynthesis of polyprenylacetone: proposal for non-enzymatic cleavage of menaquinone by reactive oxygen species

    Ueda Daijiro

    2016.3 

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  • Cyclization of squalene from both termini: identification of an onoceroid synthase and enzymatic synthesis of ambrein International conference

    Ueda Daijiro

    PACIFICHEM  2015.12 

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  • Bacillus clausiiにおけるセスタテルペン、Head-to-tailトリテルペンおよびセスクアテルペンの生合成:多機能性酵素の同定とイソプレノイド代謝物の解析

    上田 大次郎, 山鹿 宏彰, 村上 瑞気, 遠塚悠輔, 品田哲郎, 佐藤 努

    第67回日本生物工学会大会  2015.10 

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  • Biosynthesis of Sesterterpenes, Head-to-Tail Triterpenes, and Sesquarterpenes in Bacillus clausii: Identification of Multifunctional Enzymes and Analysis of Isoprenoid Metabolites International conference

    Ueda Daijiro

    KAAB International Symposium 2015  2015.9 

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  • Bacillus clausiiにおけるセスタテルペン、Head-to-tailトリテルペン、セスクアテルペンの生合成:多機能性酵素の同定とイソプレノイド代謝物の解析

    上田 大次郎, 山鹿 宏彰, 村上 瑞気, 遠塚悠輔, 品田哲郎, 佐藤 努

    第25回イソプレノイド研究会  2015.9 

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  • Bacillus clausiiにおけるセスタテルペン、Head-to-tailトリテルペン、セスクアテルペンの生合成:多機能性酵素の同定とイソプレノイド代謝物の解析

    上田 大次郎, 山鹿 宏彰, 村上 瑞気, 遠塚悠輔, 品田哲郎, 佐藤 努

    第59回香料・テルペンおよび精油化学に関する討論会  2015.9 

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  • Cyclization of squalene from both termini: identification of an onoceroid synthase and enzymatic synthesis of ambrein International conference

    Ueda Daijiro

    Inaugural Symposium of the Phytochemical Society of Asia  2015.9 

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  • Bacillus clausiiにおけるセスタテルペン、Head-to-tailトリテルペンおよびセスクアテルペンの生合成:多機能性酵素の同定とイソプレノイド代謝物の解析

    上田大次郎, 山鹿 宏彰, 村上 瑞気, 遠塚悠輔, 品田哲郎, 佐藤 努

    第50回天然物化学談話会  2015.7 

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  • Bacillus clausiiにおけるイソプレノイド生合成経路:多機能性E型プレニル鎖伸長酵素の同定とセスクアテルペン代謝物の探索

    上田 大次郎, 村上 瑞気, 山鹿 宏彰, 佐藤 努

    第11回 生合成勉強会(「生合成マシナリー」第七回若手シンポジウム)  2015.6 

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  • Bacillus clausiiにおけるイソプレノイド生合成経路:多機能性E型プレニル鎖伸長酵素の同定とセスクアテルペン代謝物の探索

    上田 大次郎, 村上 瑞気, 山鹿 宏彰, 佐藤 努

    日本農芸化学会2015年度大会  2015.3 

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  • セスクアテルペン環化酵素を基軸とするテルペン創出経路の開拓

    上田 大次郎, 山鹿 宏彰, 岡本 渉, 遠塚 悠輔, 品田 哲郎, 星野 力, 佐藤 努

    第56回天然有機化合物討論会  2014.10 

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  • 龍涎香主成分アンブレインの酵素合成、第58回香料・テルペンおよび精油化学に関する討論会

    上田 大次郎, 星野力, 佐藤努

    第58回香料・テルペンおよび精油化学に関する討論会  2014.9 

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  • スクアレンの両末端環化:オノセロイド合成酵素の初めての同定および龍涎香主成分ambreinの酵素合成

    上田大次郎, 星野力, 佐藤努

    第24回イソプレノイド研究会  2014.9 

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  • Biosynthesis of Sesterterpenes, Head-to-Tail Triterpenes, and Sesquarterpenes in Bacillus clausii: Identification of Multifunctional Enzymes and Analysis of Isoprenoid Metabolite International conference

    Ueda Daijiro

    International Symposium on Natural Products for the Future 2016  2014.9 

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  • スクアレンの両末端環化:オノセロイド合成酵素の初めての同定および龍涎香主成分ambreinの酵素合成

    上田 大次郎, 星野力, 佐藤努

    第49回天然物化学談話会  2014.7 

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  • スクアレンの両末端環化:オノセロイド合成酵素の初めての同定および龍涎香主成分ambreinの酵素合成

    上田 大次郎, 星野力, 佐藤努

    第55回新潟生化学懇話会  2014.6 

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  • スクアレンの両末端環化:オノセロイド合成酵素の初めての同定および龍涎香主成分ambreinの酵素合成

    上田大次郎, 星野力, 佐藤努

    酵素工学研究会  2014.4 

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  • スクアレンの両末端環化:オノセロイド合成酵素の初めての同定および龍涎香主成分ambreinの酵素合成

    上田大次郎, 星野力, 佐藤努

    日本農芸化学会2014年度大会  2014.3 

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  • Cyclization of squalene from both termini: identification of an onoceroid synthase and enzymatic synthesis of ambrein International conference

    Ueda Daijiro

    1st US-Japan Seminar on the Biosynthesis of Natural Products For Young Researcher  2014.3 

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  • セスクアテルペン環化酵素の部位特異的変異および非天然型トリテルペンの創出

    上田大次郎, 岡本渉, 山本彩乃, 遠塚悠輔, 品田哲郎, 仲野千秋, 佐藤 努

    第57回香料・テルペンおよび精油化学に関する討論会  2013.10 

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  • Mycobacterium属細菌由来セスクアテルペン生合成経路の解析

    上田大次郎, 小野恵梨, 尾崎真夢, 仲野千秋, 佐藤努

    第23回イソプレノイド研究会  2013.9 

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  • テトラプレニル-β-クルクメン環化酵素のさらなる能力の解析

    佐藤努, 上田大次郎, 岡本渉, 仲野千秋, 星野力

    日本農芸化学会2013年度大会  2013.3 

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Industrial property rights

Awards

  • 第28回日本セトロジー研究会最優秀発表賞

    2017.6  

    上田 大次郎

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  • 第26回イソプレノイド研究会奨励賞

    2016.9  

    上田 大次郎

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  • Poster Award (Silver), International Symposium on Natural prosucts for the Future 2016

    2016.9  

    Ueda Daijiro

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  • The Best Poster Presentation (Gold), Inaugural Symposium of the Phytochemical Society of Asia 2015.

    2015.9  

    Ueda Daijiro

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  • 第58回香料・テルペンおよび精油化学に関する討論会ベストプレゼンテーション賞

    2014.9   香料・テルペンおよび精油化学に関する討論会  

    上田 大次郎

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  • 2014年農芸化学会トピックス賞

    2014.3   日本農芸化学会  

    上田 大次郎

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  • 新潟大学学長表彰(学術研究活動において、特に顕著な成果を挙げ、学界又は社会的に高い評価を受けたもの)

    2014.3   新潟大学  

    上田 大次郎

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Research Projects

  • 昆虫由来の新型テルペン環化酵素の触媒機構解明を起点とした新規テルペンの発掘

    Grant number:23K13894

    2023.4 - 2025.3

    System name:科学研究費助成事業

    Research category:若手研究

    Awarding organization:日本学術振興会

    上田 大次郎

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    Grant amount:\4680000 ( Direct Cost: \3600000 、 Indirect Cost:\1080000 )

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  • 寄生虫由来新規天然物探索を軸としたユニークな生合成経路の開拓

    Grant number:20K15455

    2020.4 - 2022.3

    System name:科学研究費助成事業 若手研究

    Research category:若手研究

    Awarding organization:日本学術振興会

    上田 大次郎

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    Grant amount:\4160000 ( Direct Cost: \3200000 、 Indirect Cost:\960000 )

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  • Biosynthetic Engineering of Antimicrobial Isoprenoid-like Lipids for Medical and Agricultural Applications to Elucidate Physiological Functions

    2020.4 - 2021.3

    System name:Niigata University Interdisciplinary Research (U-go) Grant

    Awarding organization:Niigata University

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    Authorship:Principal investigator  Grant type:Competitive

    Grant amount:\1000000 ( Direct Cost: \1000000 )

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  • 非対称オノセロイド生合成における特異性の進化デザイン

    2019.8 - 2021.3

    System name:科研費:研究活動スタート支援

    上田 大次郎

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  • 非対称オノセロイドの生合成経路の特異性の進化デザイン(18J01646)

    2018.4 - 2018.12

    System name:科研費:特別研究員奨励費

    上田 大次郎

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    Authorship:Principal investigator  Grant type:Competitive

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  • 新型および多機能性テルペン環化酵素の解析を軸としたテルペン創出経路の拡充(15J03090)

    2015.4 - 2018.3

    System name:科研費:特別研究員奨励費

    上田 大次郎

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    Authorship:Principal investigator  Grant type:Competitive

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Teaching Experience

  • スタディ・スキルズAIc

    2023
    Institution name:新潟大学

  • スタディ・スキルズAIa

    2022
    Institution name:新潟大学

  • 農学入門II

    2022
    Institution name:新潟大学

  • 農学入門I

    2022
    Institution name:新潟大学

  • スタディ・スキルズAIIa

    2022
    Institution name:新潟大学

  • スタディ・スキルズAIIb

    2021
    Institution name:新潟大学

  • スタディ・スキルズAIb

    2021
    Institution name:新潟大学

  • 有機化学(農)

    2020
    Institution name:新潟大学

  • 微生物天然物化学

    2020
    Institution name:新潟大学

  • 有機化学実験(農)

    2019
    Institution name:新潟大学

  • 分子生命科学演習Ⅰ

    2019
    Institution name:新潟大学

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