Development of useful microbial catalysts pioneering bio-based chemical industry

• Project/Area Number: 23248014
• Research Category: Grant-in-Aid for Scientific Research (A)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Applied microbiology
• Research Institution: Kyoto University
• Principal Investigator: OGAWA Jun 京都大学, (連合)農学研究科(研究院), 教授 (70281102)
• Co-Investigator(Kenkyū-buntansha): HIBI Makoto 京都大学, 大学院農学研究科, 助教 (30432347) ; KISHINO Shigenobu 京都大学, 大学院農学研究科, 助教 (40432348) ; ANDO Akinori 京都大学, 生理化学研究ユニット, 助教 (10537765)
• Project Period (FY): 2011-04-01 – 2014-03-31
• Project Status: Completed (Fiscal Year 2013)
• Budget Amount: ¥50,310,000 (Direct Cost: ¥38,700,000、Indirect Cost: ¥11,610,000); Fiscal Year 2013: ¥14,560,000 (Direct Cost: ¥11,200,000、Indirect Cost: ¥3,360,000); Fiscal Year 2012: ¥14,560,000 (Direct Cost: ¥11,200,000、Indirect Cost: ¥3,360,000); Fiscal Year 2011: ¥21,190,000 (Direct Cost: ¥16,300,000、Indirect Cost: ¥4,890,000)
• Keywords: 酵素合成 / 微生物変換 / ジオキシゲナーゼ / アシルCoA / NADH / FAD / 水酸化反応 / 飽和化反応 / ジカルボン酸 / ジオール / オレフィン / ATP / 水酸化

Research Abstract

Organic acids, alcohol, amino acids, sugars, and lipids generated by bio-refinery processes have different chemical structures from chemicals used in modern chemical industries. Chemicals used in petro based chemical industries, such as substrates for polymer synthesis, are highly reduced compounds; while biomass derived compounds are highly oxidized ones. In this research, bio-transformation technologies modifying biomass-derived oxidized compounds to highly reduced ones are investigated. The energy-supplying systems and electron follow systems supporting the reactions are also developed. For example, dicarboxylic acid, diol, olefin production from lipids were developed together with supporting cofactor regeneration systems and energy-providing systems.

Research Products

• [Journal Article] Characteristics and biotechnology applications of aliphatic amino acid hydroxylases belonging to the Fe(II)/α-ketoglutarate-dependent dioxygenase superfamily (2014)
  • Author(s): Hibi, M., J. Ogawa
  • Journal Title: Appl. Microbiol. Biotechnol. Volume: 98(9) Issue: 9 Pages: 3869-3876
  • DOI: 10.1007/s00253-014-5620-z
  • Peer Reviewed
• [Journal Article] Hydroxy fatty acid production by Pediococcus sp (2013)
  • Author(s): Takeuchi, M., S. Kishino, K. Tanabe, A. Hirata, S.B. Park, S. Shimizu, J. Ogawa
  • Journal Title: Eur. J. Lipid Sci. Technol. Volume: 115(4) Issue: 4 Pages: 386-393
  • DOI: 10.1002/ejlt.201200414
  • Peer Reviewed
• [Journal Article] A novel l-isoleucine-4'-dioxygenase and L-isoleucine dihydroxylation cascade in Pantoea ananatis (2013)
  • Author(s): Smirnov, S.V., P.M. Sokolov, V.A. Kotlyarova, N.N. Samsonova, T. Kodera, M. Sugiyama, T. Torii, M. Hibi, S. Shimizu, K. Yokozeki, J. Ogawa
  • Journal Title: MicrobiologyOpen Volume: 2(3) Issue: 3 Pages: 471-481
  • DOI: 10.1002/mbo3.87
  • Peer Reviewed
• [Journal Article] Crystal structure of a novel N-substituted L-amino acid dioxygenase from Burkholderia ambifaria AMMD. (2013)
  • Author(s): Hui-Min Qin, Takuya Miyakawa, Min Ze Jia, Akira Nakamura, Jun Ohtsuka, You-Lin Xue, Takashi Kawashima, Takuya Kasahara, Makoto Hibi, Jun Ogawa, Masaru Tanokura
  • Journal Title: PLoS One Volume: 8 Issue: 5 Pages: e63996-e63996
  • DOI: 10.1371/journal.pone.0063996
  • Peer Reviewed
• [Journal Article] Polyunsaturated fatty acid saturation by gut lactic acid bacteria affecting host lipid composition. (2013)
  • Author(s): Kishino S, Takeuchi M, Park S, Hirata A, Kitamura N, Kunisawa J, Kiyono H, Iwamoto R, Isobe Y, Arita M, Arai H, Ueda K, Shima J, Takahashi S, Yokozeki K, Shimizu S, Ogawa J.
  • Journal Title: Proc Natl Acad Sci USA Volume: 110 Issue: 44 Pages: 17808-17813
  • DOI: 10.1073/pnas.1312937110
  • NAID: 120005341879
  • Peer Reviewed
• [Journal Article] Characterization of a trifunctional fatty acid desaturase from oleaginous filamentous fungus Mortierella alpina 1S-4 using a yeast expression system (2013)
  • Author(s): Kikukawa, H., E. Sakuradani, S. Kishino, S.B. Park, A. Ando, J. Shima, M. Ochiai, S. Shimizu, J. Ogawa
  • Journal Title: J. Biosci. Bioeng. Volume: 116(6) Issue: 6 Pages: 672-676
  • DOI: 10.1016/j.jbiosc.2013.05.023
  • NAID: 110009687829
  • Peer Reviewed
• [Journal Article] 1-Leucine 5-hydroxylase of Nostoc punctiforme is a novel type of Fe(II)/α-ketoglutarate-dependent dioxygenase that is useful as a biocatalyst (2013)
  • Author(s): Hibi, M., T. Kawashima, P.M. Sokolov, S.V. Smirnov, T. Kodera, M. Sugiyama, S. Shimizu, K. Yokozeki, J. Ogawa
  • Journal Title: Appl. Microbiol. Biotechnol. Volume: 97(6) Issue: 6 Pages: 2467-2472
  • DOI: 10.1007/s00253-012-4136-7
  • Peer Reviewed
• [Journal Article] Enzymatic synthesis of chiral amino acid sulfoxides by Fe(II)/α-ketoglutarate-dependent dioxygenase (2013)
  • Author(s): Hibi, M., T. Kawashima, H. Yajima, S.V. Smirnov, T. Kodera, M. Sugiyama, S. Shimizu, K. Yokozeki , J. Ogawa
  • Journal Title: Tetrahedron : Asymmetry Volume: 24(17) Issue: 17 Pages: 990-994
  • DOI: 10.1016/j.tetasy.2013.07.017
  • NAID: 120005323888
  • Peer Reviewed
• [Journal Article] Polyunsaturated fatty acids production and transformation by Mortierella alpina and anaerobic bacteria (2012)
  • Author(s): Jun Ogawa
  • Journal Title: European Journal of Lipid Science and Technology Volume: 114 Issue: 10 Pages: 1107-1113
  • DOI: 10.1002/ejlt.201200069
  • Peer Reviewed
• [Journal Article] Construction of microbial platform for an energy-requiring bioprocess : practical 2'-deoxyribonucleoside production involving a C-C coupling reaction with high energy substrates (2012)
  • Author(s): Horinouchi, N., T. Sakai, T. Kawano, S. Matsumoto, M. Sasaki, M. Hibi, J. Shima, S. Shimizu, J. Ogawa
  • Journal Title: Microbial Cell Factories Volume: 11(82) Issue: 1
  • DOI: 10.1186/1475-2859-11-82
  • Peer Reviewed
• [Journal Article] Oxidative pyrimidine metabolism in Rhodococcus erythropolis useful for valuable nucleoside synthesis : Discovery of a novel amidohydorolase, ureidomalonase (2012)
  • Author(s): Horinouchi, N., C.L. Soon, S. Shimizu, J. Ogawa
  • Journal Title: Biocat. Agri. Biotechnol. Volume: 1(3) Issue: 3 Pages: 264-266
  • DOI: 10.1016/j.bcab.2012.03.011
  • NAID: 120004161054
  • Peer Reviewed
• [Journal Article] A novel Fe(II)/α-ketoglutarate-dependent dioxygenase from Burkholderia ambifaria has β-hydroxylating activity of N-succinyl L-leucine (2012)
  • Author(s): Hibi, M., T. Kawashima, T. Kasahara, P.M. Sokolov, S.V. Smirnov, T. Kodera, M. Sugiyama, S. Shimizu, K. Yokozeki, J. Ogawa
  • Journal Title: Lett. Appl. Microbiol. Volume: 55(6) Issue: 6 Pages: 414-419
  • DOI: 10.1111/j.1472-765x.2012.03308.x
  • Peer Reviewed
• [Journal Article] Extracellular oxidases of Cerrena sp. complementarily functioning in artificial dye decolorization including laccase, manganese peroxidase, and novel versatile peroxidases (2012)
  • Author(s): Hibi, M., S. Hatahira, M. Nakatani, K. Yokozeki, S. Shimizu, J. Ogawa
  • Journal Title: Biocat. Agri. Biotechnol. Volume: 1(3) Issue: 3 Pages: 220-225
  • DOI: 10.1016/j.bcab.2012.03.003
  • NAID: 120004247249
  • Peer Reviewed
• [Journal Article] β-Aryl-β-amino acid aminotransferase from Variovorax sp. JH2 is useful for enantioselective β-phenylalanineproduction (2012)
  • Author(s): Hibi, M., J. Mano, T. Hagishita, J. Shima, S. Shimizu, J. Ogawa
  • Journal Title: Biocat. Agri. Biotechnol. Volume: 1(3) Issue: 3 Pages: 253-258
  • DOI: 10.1016/j.bcab.2012.04.001
  • Peer Reviewed
• [Journal Article] バイオプラ最前線-バイオマスからのモノマー生産を支援するバイオリピッドプラットフォームの構築- (2012)
  • Author(s): 小川順,櫻谷英治,岸野重信,日比慎,安藤晃規
  • Journal Title: バイオプラジャーナル Volume: 44 Pages: 13-19
  • NAID: 40019193378
• [Journal Article] バイオマスからのモノマー生産を支援するバイオリピッドプラットフォームの構築- (2012)
  • Author(s): 小川 順
  • Journal Title: バイオプラジャーナル Volume: 44 Pages: 13-19
• [Journal Article] A novel family of bacterial dioxygenases that catalyse the hydroxylation of free L-amino acids. FEMS Microbiol. Lett., 331 (2), 97-104 (2012). (2012)
  • Author(s): Smirnov, S.V.
  • Journal Title: FEMS Microbiol. Lett. Volume: 331 Issue: 2 Pages: 97-104
  • DOI: 10.1111/j.1574-6968.2012.02558.x
  • Peer Reviewed
• [Journal Article] Novel multi-component enzyme machinery in lactic acid bacteria catalyzing C=C double bond migration useful for conjugated fatty acid synthesis (2011)
  • Author(s): Kishino, S., S.B. Park, M. Takeuchi, K. Yokozeki, S. Shimizu, J. Ogawa
  • Journal Title: Biochem. Biophys. Res. Commun. Volume: 416(1-2) Issue: 1-2 Pages: 188-193
  • DOI: 10.1016/j.bbrc.2011.11.022
  • Peer Reviewed
• [Journal Article] Linoleic Acid Isomerase in Lactobacillus plantarum AKU1009a Proved to Be a Multi-Component Enzyme System Requiring Oxidoreduction Cofactors (2011)
  • Author(s): Kishino, S., J. Ogawa, K. Yokozeki, S. Shimizu
  • Journal Title: Bioscience, Biotechnology, and Biochemistry Volume: 75 Issue: 2 Pages: 318-322
  • DOI: 10.1271/bbb.100699
  • NAID: 10027897895
  • ISSN: 0916-8451, 1347-6947
  • Peer Reviewed
• [Presentation] Development of multi-component enzyme systems for future chemical industry (2013)
  • Author(s): J. Ogawa, M. Hibi, S. Kishino, N. Horinouchi1, A. Ando, E. Sakuradani1, S. Shimizu
  • Organizer: 2013 KSBB Spring Meeting and International Symposium
  • Place of Presentation: Gwangju, Korea
  • Invited
• [Presentation] Screening and application of microbial oxidase and oxygense (2013)
  • Author(s): J. Ogawa, M. Hibi, K. Yokozeki, S. Takahashi, S. Shimizu
  • Organizer: 104th AOCS Annual Meeting & Expo
  • Place of Presentation: Montreal, Canada
  • Invited
• [Presentation] Characterization of acyl-CoA synthetase genes from oleaginous fungus Mortierella alpina 1S-4 (2013)
  • Author(s): E. Sakuradani, T. Asaoka, H. Kikukawa, T. Okuda, A. Ando, M. Ochiai1, J. Ogawa
  • Organizer: 104th AOCS Annual Meeting & Expo
  • Place of Presentation: Montreal, Canada
  • Invited
• [Presentation] Microbial Fe(II)/α-ketoglutarate-dependent dioxygenases for valuable amino acid productions (2013)
  • Author(s): M. Hibi, S. Shimizu, S. Takahashi1, J. Ogawa
  • Organizer: Biotrans 2013
  • Place of Presentation: Manchester, UK
• [Presentation] Enzymatic chiral alcohol synthesis using oxygenases and hydratases (2013)
  • Author(s): J. Ogawa, M. Hibi, S. Kishino, S. Shimizu
  • Organizer: 17th German-Japanese Workshop on Enzyme Technology
  • Place of Presentation: Hamburg, Germany
  • Invited
• [Presentation] Development of platform technologies and screening of module enzymes for multi-component enzyme systems requiring energy supply (2013)
  • Author(s): J. Ogawa, S. Kishino, M. Hibi, N. Horinouchi, K. Yokozeki, S. Takahashi, S. Shimizu
  • Organizer: Enzyme Engineering XXII
  • Place of Presentation: Toyama, Japan
  • Invited
• [Presentation] Lactobacillus plantarumの脂肪酸代謝を活用した実用化レベルでの水酸化脂肪酸生産 (2013)
  • Author(s): 福永 健太
  • Organizer: 日本農芸化学会2013年度大会
  • Place of Presentation: 仙台
• [Presentation] カルボン酸還元能を有する嫌気性細菌の探索 (2013)
  • Author(s): 中谷 友樹
  • Organizer: 日本農芸化学会2013年度大会
  • Place of Presentation: 仙台
• [Presentation] Microbial Oxygenases as Catalysts for Fine Chemical Synthesis (2012)
  • Author(s): Ogawa, J
  • Organizer: 103rd AOCS Annual Meeting & Expo
  • Place of Presentation: Long Beach, CA, USA
• [Presentation] Application of microbial oxidizing enzymes for fine chemical synthesis and environmental Biotechnology (2012)
  • Author(s): Ogawa, J
  • Organizer: The 12th Japan-China-Korea Joint Symposium on Enzyme Engineering
  • Place of Presentation: Kanazawa, Japan
• [Presentation] Microbial Oxygenases as Catalysts for Fine Chemical Synthesis (2012)
  • Author(s): Ogawa, J.
  • Organizer: 103ｒｄ AOCS Annual Meeting & Expo
  • Place of Presentation: Long Beach, CA, USA
  • Invited
• [Presentation] Novel Enzyme in Lactic Acid Bacteria for Fatty Acid Conversion to Hydroxy Fatty Acids (2012)
  • Author(s): Kishino, S.
  • Organizer: 103ｒｄ AOCS Annual Meeting & Expo
  • Place of Presentation: Long Beach, CA, USA
  • Invited
• [Presentation] Application of microbial oxidizing enzymes for fine chemical synthesis and environmental biotechnology (2012)
  • Author(s): Ogawa, J.
  • Organizer: The 12th Japan-China-Korea Joint Symposium on Enzyme Engineering
  • Place of Presentation: Kanazawa, Japan
• [Presentation] Development of Microbial Multi-component Enzyme Systems (2011)
  • Author(s): J. Ogawa
  • Organizer: IUMS 2011 XIII International Congress of Bacteriology and Applied Microbiology
  • Place of Presentation: 札幌
  • Year and Date: 2011-09-07
• [Presentation] Development of Microbial Multi-component Enzyme Systems (2011)
  • Author(s): J.Ogawa, et.al.
  • Organizer: IUMS 2011 XIII International Congress of Bacteriology and Applied Microbiology
  • Place of Presentation: 札幌コンベンションセンター(招待講演)
  • Year and Date: 2011-09-07
• [Remarks]
  • URL: http://www.hakko.kais.kyoto-u.ac.jp/