Development of microbial catalyst catalyzing high shikimate production from quinate

• Project/Area Number: 19380050
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Applied microbiology
• Research Institution: Yamaguchi University
• Principal Investigator: ADACHI Osao Yamaguchi University, 名誉教授 (20027189)
• Co-Investigator(Kenkyū-buntansha): AKAKABE Yoshihiko 山口大学, 農学部, 准教授 (20274186) ; SHINAGAWA Emiko 宇部工業高等専門学校, 物質工学科, 教授 (20116726)
• Project Period (FY): 2007 – 2009
• Project Status: Completed (Fiscal Year 2009)
• Budget Amount: ¥20,410,000 (Direct Cost: ¥15,700,000、Indirect Cost: ¥4,710,000); Fiscal Year 2009: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000); Fiscal Year 2008: ¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000); Fiscal Year 2007: ¥13,650,000 (Direct Cost: ¥10,500,000、Indirect Cost: ¥3,150,000)
• Keywords: 酢酸菌 / 酸化発酵 / シキミ酸 / コーヒー麹 / タミフル / キナ酸の製造 / シキミ酸の製造 / コーヒー粕麹 / 固定化触媒

Research Abstract

A novel strategy preparing high shikimic acid with high efficiency with developed microbial enzymes from fungi and acetic acid bacteria has finally completed during three years of investigation supported by this grant. Coffee pulp koji facilitated strong formation of chlorogenic acid hydrolase and yielded quinic acid from coffee pulp easier than any other methods so far reported. Quinic acid was converted by two enzyme systems of acetic acid bacteria, oxidative fermentation of 3-dehydroshikimate from quinic acid and asymmetric reduction yielding shikimic acid from 3-dehydroshikimate were so successful. The fruitful outcomes in this project must help people from pandemic flu through plentiful supply of Tamiflu synthesized from shikimic acid provided in this project.

Research Products

• [Journal Article] Purification and characterization of membrane-bound 3-dehydroshikimate dehydratase from Gluconobacter oxydans IFO 3244, a new enzyme catalyzing extracellular protocatechuate formation. (2010)
  • Author(s): E. Shinagawa, O. Adachi, Y. Ano, T. Yakushi, K. Matsushita
  • Journal Title: Biosci. Biotechnol. Biochem. 74(in press)
  • NAID: 10027555519
• [Journal Article] Characterizationof thermotolerant Acetobacter pasteurianus strains and their quinoprotein alcohol dehydrogenases. (2010)
  • Author(s): W. Kanchanarach, G. Theeragool, T. Yakushi, H. Toyama, O. Adachi, K. Matsushita
  • Journal Title: Appl. Microbiol. Biotechnol. 85 Pages: 741-751
• [Journal Article] Purification and characterization of membrane-bound 3-dehydroshikimate dehydratase from Gluconobacter oxydns IFO 3244, a new enzyme catalyzing extracellualr protocatechuate formation (2010)
  • Author(s): 品川恵美子
  • Journal Title: Biosci. Biotechnol. Biochem. 74(印刷中)
  • Peer Reviewed
• [Journal Article] Screening of thermotolerant Gluconobacter strains for production of 5-keto-D-gluconic acid and disruption of flavin adenine dinucleotide-containing D-gluconate dehydrogenase. (2009)
  • Author(s): I. Saichana, D. Moonmangmee, O. Adachi, K. Matsushita, H. Toyama
  • Journal Title: Appl. Environ. Microbiol. 75 Pages: 4240-4247
• [Journal Article] Solubilization, purification, and properties of membrane-bound D-glucono-d-lactone hydrolase from Gluconobacter oxydans. (2009)
  • Author(s): E. Shinagawa, Y. Ano, T. Yakushi, O. Adachi, K. Matsushita
  • Journal Title: Biosci. Biotechnol. Biochem. 73 Pages: 241-244
• [Journal Article] A tightly bound quinone functions in the ubiquinone reaction sites of quinoprotein alcohol dehydrogenase of an acetic acid bacterium, Gluconobacter suboxydans. (2008)
  • Author(s): K. Matsushita, Y. Kobayashi, M. Mizuguchi, H. Toyama, O. Adachi, K. Sakamoto, H. Miyoshi
  • Journal Title: Biosci. Biotechnol. Biochem. 72 Pages: 2723-2731
  • NAID: 10027533332
• [Journal Article] Coffee pulp koji of Aspergillus sojae as stable immobilized catalyst of chlorogenate hydrolase. (2008)
  • Author(s): O. Adachi, Y. Ano, Y. Akakabe, E. Shinagawa, K. Matsushita
  • Journal Title: Appl. Microbiol. Biotechnol. 81 Pages: 143-151
• [Journal Article] Purification and properties of two different dihydroxyacetone reductases in Gluconobacter suboxydans grown on glycerol. (2008)
  • Author(s): O. Adachi, Y. Ano, E. Shinagawa, K. Matsushita
  • Journal Title: Biosci. Biotechnol. Biochem. 72 Pages: 2124-2132
  • NAID: 10027531003
• [Journal Article] A novel 3-dehydroquinate dehydratase catalyzing extracellular formation of 3-dehydroshikimate by oxidative fermentation of Gluconobacter oxydans IFO 3244. (2008)
  • Author(s): O. Adachi, Y. Ano, H. Toyama, K. Matsushita
  • Journal Title: Biosci. Biotechnol. Biochem. 72 Pages: 1472-1482
  • NAID: 10027528553
• [Journal Article] Energy metabolism of a unique acetic acid bacterium, Asaia bogorensis, that lacks ethanol oxidation activity. (2008)
  • Author(s): Y. Ano, H. Toyama, O. Adachi, K. Matsushita
  • Journal Title: Biosci. Biotechnol. Biochem. 72 Pages: 989-997
  • NAID: 10027526551
• [Journal Article] Formaldehyde elimination with formaldehyde and formate oxidase in membrane of acetic acid bacteria (2008)
  • Author(s): E. Shinagawa, H. Toyama, K. Matsushita, P. Tuitemwong, G. Theeragool, O. Adachi
  • Journal Title: J. Biosci. Bioeng. 105 Pages: 292-295
  • NAID: 110006632563
• [Journal Article] Disruption of quinoprotein ethanol dehydrogenase gene and adjacent genes in Pseudomonas putida HK5. (2008)
  • Author(s): W. Promden, A.S. Vangnai, P. Pongsawasdi, O. Adachi, K. Matsuthita, H. Toyama
  • Journal Title: FEMS Microbiol Lett. 280 Pages: 203-209
• [Journal Article] Distinct physiological roles of two membrane-bound dehydrogenases responsible for D-sorbitol oxidation in Gluconobacter frateurii. (2008)
  • Author(s): W. Soemphol, O. Adachi, K. Matsushita, H. Toyama
  • Journal Title: Biosci. Biotechnol. Biochem. 72 Pages: 842-850
  • NAID: 10027525958
• [Journal Article] The occurrence of a novel NADH dehydrogenase, distinct from the old yellow enzyme, in Gluconobacter strains. (2008)
  • Author(s): E. Shinagawa, Y. Ano, O. Adachi, K. Matsushita
  • Journal Title: Biosci. Biotechnol. Biochem. 72 Pages: 260-264
  • NAID: 10027523610
• [Journal Article] A novel 3-dehydroquinate dehydratase catalyzing extracellular formation of 3-dehydroshiikimate by oxidative fermentation of Gluconobacter oxydans IFO 3244 (2008)
  • Author(s): O. Adachi, ら
  • Journal Title: Biosci. Biotechnol. Biochem. 72 Pages: 1475-1482
  • Peer Reviewed
• [Journal Article] Coffee pulp koji of Aspergillus sojae as stable immobilized catalyst of chlorogenate hydrolase (2008)
  • Author(s): O. Adachi, ら
  • Journal Title: Appl. Microbiol. Biotechnol. 81 Pages: 143-151
  • Peer Reviewed
• [Journal Article] High Induction of Chlorogenate Hydrolase in Fungi and Coffee Pulp Koji Preparation for Ouinate and Caffate Production (2008)
  • Author(s): O. Adachi, ら
  • Journal Title: Biosci.Biotechnol.Biochem. 71(印刷中)
  • Peer Reviewed
• [Journal Article] Membrane-bound, 2-keto-D-gluconate-yielding D-gluconate dehydrogenase from Gluconobacter dioxyacetonicus IFO 2171: Molecular properties and gene disruption. (2007)
  • Author(s): H. Toyama, N. Furuya, I. Saichana, Y. Ano, O. Adachi, K. Matsushita
  • Journal Title: Appl. Environ. Microbiol. 73 Pages: 6551-6556
• [Journal Article] Preparation of enzymes required for enzymatic quantification of 5-keto-D-gluconate and 2-keto-D-gluconate. (2007)
  • Author(s): I. Saichana, Y. Ano, O. Adachi, K. Matsushita, H. Toyama
  • Journal Title: Biosci. Biotechnol. Biochem. 71 Pages: 2478-2486
  • NAID: 10027519914
• [Journal Article] L-Sorbose reductse and its transcriptional regulator involved in L-sorbose utilization of Gluconobacter frateurii. (2007)
  • Author(s): W. Soemphol, H. Toyama, D. Moonmangmee, O. Adachi, K. Matsushita
  • Journal Title: J. Bacteriol. 189 Pages: 4800-4808
• [Journal Article] Factors required for the catalytic reaction of PqqC/D which produces pyrroloquinoline quinone. Biochem. (2007)
  • Author(s): H. Toyama, E. Nishibayashi, M. Saeki, O. Adachi, K. Matsushita
  • Journal Title: Biophys. Res. Commun. 354 Pages: 290-295
• [Presentation] 膜結合型デヒドロシキミ酸デヒドラターゼの発見、酵素の精製と性質 (2011)
  • Author(s): 品川恵美子、足立収生、阿野嘉孝、薬師寿治、松下一信
  • Organizer: 日本農芸化学会大会
  • Place of Presentation: 東大駒場キャンパス、東京
• [Presentation] 酢酸菌の固定化酵素を用いたシキミ酸製造法の検討 (2011)
  • Author(s): 足立収生、阿野嘉孝、品川恵美子、薬師寿治、松下一信
  • Organizer: 日本農芸化学会大会
  • Place of Presentation: 東大駒場キャンパス、東京
• [Presentation] 膜結合型デヒドロシキミ酸デヒドラターゼの発見、酵素の精製と性質 (2010)
  • Author(s): 足立収生
  • Organizer: 日本農芸化学会大会
  • Place of Presentation: 東大駒場キャンパス
  • Year and Date: 2010-03-30
• [Presentation] 酢酸菌の固定化酵素を用いたシキミ酸製造法の検討 (2010)
  • Author(s): 足立収生
  • Organizer: 日本農芸化学会大会
  • Place of Presentation: 東大駒場キャンパス
  • Year and Date: 2010-03-28
• [Presentation] 糸状菌のクロロゲン酸水解酵素の誘導、酵素の精製とキナ酸製造への応用 (2010)
  • Author(s): 足立収生、阿野嘉孝、品川恵美子、松下一信
  • Organizer: 日本農芸化学会大会
  • Place of Presentation: 名城大学、名古屋市
• [Presentation] コーヒー粕からシキミ酸およびシキミ酸経路代謝中間体の高速・高効率製造法 (2009)
  • Author(s): 松下一信、足立収生
  • Organizer: 科学技術振興機構新技術開発説明会
  • Place of Presentation: (独)科学技術振興機構、東京
  • Year and Date: 2009-10-23
• [Presentation] Quinic acid prodouction from coffee pulp by fungal enzyme and subsequent conversion of quinic acid to shikimic acid by two enzymatic systems of acetic acid bacteria. (2009)
  • Author(s): O. Adachi, T. Yakushi, K. Matsushita
  • Organizer: The 15th German-Japanese Workshop on Enzyme Technology
  • Place of Presentation: Rostoc University, Germany
• [Presentation] he Japanese traditional applied microbiology may contribute to the Argentine (2009)
  • Author(s): O. Adachi, K. Matsushita
  • Organizer: Japan-Argentina Workshop "Bioscience and Biotechnology for the promotion of Agriculture and Food Production"
  • URL: http://www.jst.go.jp/sicp/ws2009_argentina/presentation/day1_08.pdf
  • Place of Presentation: Buenos Aires, Argentina.
• [Presentation] Quinic acid prodouction from coffee pulp by fungal enzyme and subsequent conversion of quinic acid to shikimim acid by two enzymatic systems of acetic acid bacteria (2009)
  • Author(s): O.Adachi
  • Organizer: The 15^<th> German-Japanese Workshop on Enzyme Technology
  • Place of Presentation: Rostoc Univ, Germany
• [Presentation] The Japanese traditional applied microbiology may contribute to the Argentine (2009)
  • Author(s): O.Adachi
  • Organizer: Japan-Argentina Workship "Bioscience and Biotechnology for the promotion of Agriculture and Food Production"
  • Place of Presentation: Buenos Aires, Argentina
• [Presentation] コーヒー粕からシキミ酸およびシキミ酸経路代謝中間体の高速・高効率製造法 (2008)
  • Author(s): 足立収生
  • Organizer: 利学技術振興機構新技術説明会
  • Place of Presentation: 東京JST本部講堂
  • Year and Date: 2008-10-23
• [Presentation] 糸状菌のクロロゲン酸水解酵素の誘導、酵素の精製とキナ酸製造への応用 (2007)
  • Author(s): 足立 収生, ら
  • Organizer: 2008日本農芸化学会
  • Place of Presentation: 名城大学
  • Year and Date: 2007-03-27
• [Book] Biooxidation with PQQ-and FAD-dependent dehydrogenases. In“Modern Biooxidations-Enzymes, Reactions and Applications"ed (2007)
  • Author(s): O. Adachi, Y. Ano, H. Toyama, K. Matsushita
  • Publisher: by R. D. Schmid and V. Urlacher(Wiley-VCH)
• [Patent(Industrial Property Rights)] コーヒー粕麹による有用物質の製造法 (2009)
  • Inventor(s): 松下一信、足立収生
  • Industrial Property Rights Holder: 山口大学
  • Filing Date: 2009-02-03
• [Patent(Industrial Property Rights)] キナ酸および/またはカフェ酸の製造法 (2008)
  • Inventor(s): 松下 一信, 足立 収生
  • Industrial Property Rights Holder: 山口大学
  • Industrial Property Number: 2008-049837
  • Filing Date: 2008-02-29