Search for novel families of terpene cyclases from bacteria and analyses of physiological functions and bioactivities of C35 terpenes

• Project/Area Number: 21780109
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Bioproduction chemistry/Bioorganic chemistry
• Research Institution: Niigata University
• Principal Investigator: SATO Tsutomu Niigata University, 自然科学系, 准教授 (80334655)
• Project Period (FY): 2009 – 2010
• Project Status: Completed (Fiscal Year 2010)
• Budget Amount: ¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000); Fiscal Year 2010: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000); Fiscal Year 2009: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
• Keywords: テルペン / テルペン環化酵素 / Mycobacterium / 枯草菌 / イソプレノイド / プレニル鎖伸長酵素 / プレニル鎖還元酵素 / 生合成

Research Abstract

A bifunctional Z-prenyltransferase that preferentially synthesize C_<35> or C_<50> products was found from the study on the mycobacterial C_<35> terpenes. The structure of two novel C_<35> terpenes suggested that a prenyl reductase reducing both E and Z prenyl residues was responsible for the biosynthesis of C_<35> terpenes. On the other hand, a novel family of terpene cyclases and tetraprenyl-β-curcumene cyclase from Bacillus subtilis could be identified by the in vitro enzymatic reaction.

Research Products

• [Journal Article] Characterization of the Rv3378c gene product,a new diterpene synthase for producingtuberculosinol and (13R, S)-isotuberculosinol(nosyberkol), from the Mycobacteriumtuberculosis H37Rv genome. (2011)
  • Author(s): Chiaki NAKANO, Takahiro OOTSUKA,Kazutoshi TAKAYAMA, Toshiaki MITSUI,Tsutomu SATO, Tsutomu HOSHINO
  • Journal Title: Biosci.Biotechnol.Biochem. 75 Pages: 75-81
  • Peer Reviewed
• [Journal Article] Characterization of the Rv3378c gene product, a new diterpene synthase for producing tuberculosinol and (13R, S)-isotuberculosinol (nosyberkol), from the Mycobacterium tuberculosis H37Rv genome. (2011)
  • Author(s): 仲野千秋
  • Journal Title: Biosci.Biotechnlol.Biochem. Volume: 75 Pages: 75-81
  • Peer Reviewed
• [Journal Article] Insight into C35-terpene biosyntheses bynon-pathogenic Mycobacterium species:functional analyses of threeZ-prenyltransferases and identification ofdehydroheptaprenylcyclines. (2010)
  • Author(s): Tsutomu SATO, Kazuo TAKIZAWA, YurikoORITO, Hanayo KUDO, Tsutomu HOSHINO
  • Journal Title: ChemBioChem 11 Pages: 1874-1881
  • Peer Reviewed
• [Journal Article] Substrate specificity of theCYC2 enzyme from Kitasatospora griseola:production of sclarene, biformene and novelbicyclic diterpenes by the enzymatic reactionsof labdane- and halimane-type diterpenediphosphates. (2010)
  • Author(s): Chiaki NAKANO, Tsutomu HOSHINO, TsutomuSATO, Tomonobu TOYOMASU, Tohru DAIRI, Takeshi SASSA
  • Journal Title: Tetrahedron Lett. 51 Pages: 125-128
  • Peer Reviewed
• [Journal Article] Novel compounds of octahydroheptaprenylmycolic acyl ester and monocyclic C35-terpene,heptaprenylcycline B, from nonpathogenicMycobacterium species. (2010)
  • Author(s): Tsutomu SATO, Ryosuke TAKAGI, YurikoORITO, Eri ONO, Tsutomu HOSHINO
  • Journal Title: Biosci.Biotechnol.Biochem. 74 Pages: 147-151
  • Peer Reviewed
• [Journal Article] Insight into C_<35>-terpene biosyntheses by non-pathogenic Mycobacterium species : functional analyses of three Z-prenyltransferases and identification of dehydroheptaprenylcyclines. (2010)
  • Author(s): 佐藤努
  • Journal Title: ChemBioChem Volume: 11 Pages: 1874-1881
  • Peer Reviewed
• [Journal Article] Substrate specificity of the CYC2 enzyme from Kitasatospora griseola : production of sclarene, biformene and novel bicyclic diterpenes by the enzymatic reactions of labdane- and halimane-type diterpene diphosphates (2010)
  • Author(s): 仲野千秋
  • Journal Title: Tetrahedron Lett. 51 Pages: 125-128
  • Peer Reviewed
• [Journal Article] Novel Compounds of Octahydroheptaprenyl Mycolic Acyl Ester and Monocyclic C_<35>-Terpene, Heptaprenylcycline B, from Non-Pathogenic Mycobac terium Species (2010)
  • Author(s): 佐藤努
  • Journal Title: Bioscu.Biotechnol.Biochem. 74 Pages: 147-151
  • NAID: 10027550432
  • Peer Reviewed
• [Presentation] 枯草菌由来C_35テルペンの生合成:新型テルペン環化酵素のテトラプレニル-β-クルクメン合成酵素の同定 (2011)
  • Author(s): 吉田悟
  • Organizer: 日本農芸化学会
  • Place of Presentation: 京都
  • Year and Date: 2011-03-26
• [Presentation] 枯草菌由来C_35テルペンの生合成:テトラプレニル-β-クルクメン環化酵素のin vitro 反応による同定と基質特異性 (2011)
  • Author(s): 星野紘子
  • Organizer: 日本農芸化学会
  • Place of Presentation: 京都
  • Year and Date: 2011-03-26
• [Presentation] 豚肝ラノステロール合成酵素:オキシドスクアレン19 位のバルクサイズが環化反応に及ぼす影響 (2011)
  • Author(s): 阿部奈緒美
  • Organizer: 日本農芸化学会
  • Place of Presentation: 京都
  • Year and Date: 2011-03-26
• [Presentation] 28-noroxidosqualene とβ-アミリン合成酵素との酵素反応 (2011)
  • Author(s): 山口雄生
  • Organizer: 日本農芸化学会
  • Place of Presentation: 京都
  • Year and Date: 2011-03-26
• [Presentation] ミドリサンゴ由来β-amyrin合成酵素F413残基の機能解析 (2011)
  • Author(s): 伊藤遼介
  • Organizer: 日本農芸化学会
  • Place of Presentation: 京都
  • Year and Date: 2011-03-26
• [Presentation] 枯草菌由来C_<35>テルペンの生合成:新型テルペン環化酵素のテトラプレニル-β-クルクメン合成酵素の同定 (2011)
  • Author(s): 吉田悟
  • Organizer: 日本農芸化学会
  • Place of Presentation: 京都
  • Year and Date: 2011-03-26
• [Presentation] 枯草菌由来C_<35>テルペンの生合成:テトラプレニル-β-クルクメン環化酵素のin vitro反応による同定と基質特異性 (2011)
  • Author(s): 星野紘子
  • Organizer: 日本農芸化学会
  • Place of Presentation: 京都
  • Year and Date: 2011-03-26
• [Presentation] 豚肝ラノステロール合成酵素:オキシドスクアレン19位のバルクサイズが環化反応に及ぼす影響 (2011)
  • Author(s): 阿部奈緒美
  • Organizer: 日本農芸化学会
  • Place of Presentation: 京都
  • Year and Date: 2011-03-26
• [Presentation] 28-noroxidosqualeneとβ-アミリン合成酵素との酵素反応 (2011)
  • Author(s): 山口雄生
  • Organizer: 日本農芸化学会
  • Place of Presentation: 京都
  • Year and Date: 2011-03-26
• [Presentation] 非病原性マイコバクテリアに存在するユニークなC_35テルペンの生合成:Z型プレニルトランスフェラーゼの機能解析とデヒドロヘプタプレニルサイクリンの同定 (2010)
  • Author(s): 佐藤努
  • Organizer: 第20回ドリコールおよびイソプレノイド研究会例会
  • Place of Presentation: 名古屋
  • Year and Date: 2010-10-09
• [Presentation] 非病原性マイコバクテリアに存在するユニークなC_<35>テルペンの生合成:Z型プレニルトランスフェラーゼの機能解析とデヒドロヘプタプレニルサイクリンの同定 (2010)
  • Author(s): 佐藤努
  • Organizer: 第20回ドリコールおよびイソプレノイド研究会例会
  • Place of Presentation: 名古屋
  • Year and Date: 2010-10-09
• [Presentation] イネ由来のトリテルペン環化酵素 (2010)
  • Author(s): 伊藤遼介
  • Organizer: 第52回天然有機化合物討論会
  • Place of Presentation: 静岡
  • Year and Date: 2010-09-30
• [Presentation] 非病原性Mycobacterium属由来のC3_5テルペン生合成酵素の探索 (2010)
  • Author(s): 滝沢和央
  • Organizer: 日本農芸化学会
  • Place of Presentation: 東京
  • Year and Date: 2010-03-29
• [Presentation] ミドリサンゴ由来のβ-アミリン合成酵素の酵素学的諸性質 (2010)
  • Author(s): 伊藤遼介
  • Organizer: 日本農芸化学会
  • Place of Presentation: 東京
  • Year and Date: 2010-03-29
• [Presentation] Mycobacterium tuberculosis H37Rv3378c 酵素の再検討 (2010)
  • Author(s): 大塚崇弘
  • Organizer: 日本農芸化学会
  • Place of Presentation: 東京
  • Year and Date: 2010-03-29
• [Presentation] 非病原性Mycobacterium属由来のC_<35>テルペン生合成酵素の探索 (2010)
  • Author(s): 滝沢和央
  • Organizer: 日本農芸化学会
  • Place of Presentation: 東京
  • Year and Date: 2010-03-29
• [Presentation] Mycobacterium tuberculosis H37 Rv3378c酵素の再検討 (2010)
  • Author(s): 大塚崇弘
  • Organizer: 日本農芸化学会
  • Place of Presentation: 東京
  • Year and Date: 2010-03-29
• [Presentation] イネ由来のトリテルペン合成酵素AK070534の機能解析 (2010)
  • Author(s): 星野力
  • Organizer: 日本農芸化学会
  • Place of Presentation: 東京
  • Year and Date: 2010-03-28
• [Presentation] イネ由来のトリテルペン合成酵素AKO70534の機能解析 (2010)
  • Author(s): 星野力
  • Organizer: 日本農芸化学会
  • Place of Presentation: 東京
  • Year and Date: 2010-03-28
• [Presentation] イネ由来のシクロアルテノールおよびパルケオール合成酵素 (2009)
  • Author(s): 星野力
  • Organizer: 第53回香料・テルペンおよび精油化学に関する討論会
  • Place of Presentation: 奈良
  • Year and Date: 2009-11-08
• [Presentation] 細菌由来のC_35テルペンの探索と生合成研究 (2009)
  • Author(s): 佐藤努
  • Organizer: 第53回香料・テルペンおよび精油化学に関する討論会
  • Place of Presentation: 奈良
  • Year and Date: 2009-11-08
• [Presentation] 細菌由来のC_<35>テルペンの探索と生合成研究 (2009)
  • Author(s): 星野力
  • Organizer: 第53回香料・テルペンおよび精油化学に関する討論会
  • Place of Presentation: 奈良
  • Year and Date: 2009-11-08
• [Presentation] Biosynthesis of a novel cyclicC35-terpene by the cyclization of a Z-typeC_35-polyprenyl diphosphate obtained from anonpathogenic Mycobacterium species (2009)
  • Author(s): 佐藤努
  • Organizer: TERPNET 2009
  • Place of Presentation: 東京
  • Year and Date: 2009-05-26
• [Presentation] Biosynthesis of a novel cyclic C_<35>-terpene by the cyclization of a Z-type C_<35>-polyprenyl diphosphate obtained from a nonpathogenic Mycobacterium species (2009)
  • Author(s): 佐藤努
  • Organizer: TERPNET 2009
  • Place of Presentation: 東京
  • Year and Date: 2009-05-26
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