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Development of enzymatic resolution process of pantolactone by fungal lactonase

Research Project

Project/Area Number 08556013
Research Category

Grant-in-Aid for Scientific Research (A)

Allocation TypeSingle-year Grants
Section展開研究
Research Field 応用微生物学・応用生物化学
Research InstitutionKYOTO UNIVERSITY

Principal Investigator

SHIMIZU Sakayu  Kyoto Univ.Agr.Professor, 農学研究科, 教授 (70093250)

Co-Investigator(Kenkyū-buntansha) OGAWA Jun  Kyoto Univ.Agr.Assistant Prof., 農学研究科, 助手 (70281102)
KATAOKA Michihiko  Kyoto Univ.Agr.Assistant Prof., 農学研究科, 助手 (90252494)
KOBAYASHI Michihiko  Kyoto Univ.Agr.Senior Lecturer, 農学研究科, 講師 (70221976)
SAKAMOTO Keiji  Fuji Chemical Industries.Researcher, 研究所, 主任研究員
Project Period (FY) 1996 – 1997
Project Status Completed (Fiscal Year 1997)
Budget Amount *help
¥10,000,000 (Direct Cost: ¥10,000,000)
Fiscal Year 1997: ¥2,900,000 (Direct Cost: ¥2,900,000)
Fiscal Year 1996: ¥7,100,000 (Direct Cost: ¥7,100,000)
KeywordsLactonase / Fusarium oxysporum / Pantolactone / Enzymatic resolution / Immobilized enzyme
Research Abstract

A novel enzymatic process for the optical resolution of racemic pantolactone through the stereospecific hydrolysis of D-pantolactone by lactonohydrolase of Fusarium oxysporum is developed. F.oxysporum showed high productivity of the enzyme and the cells containing the enzyme could be used repeatedly for this hydrolysis reaction. D-Pantolactone in a racemic mixture of pantolactone (700mg/ml) was almost stoichiometrically hydrolyzed to D-pantoic acid on incubation with F.oxysporum cells for 24h under conditions in which the pH was automatically maintained at 7.0 (optical purity for D-pantoic acid, 96% e.e.). In practice the hydrolysis of the D-pantolactone in a racemic mixture is achieved by immobilized cells of F.oxysporum as the catalyst. Stable catalysts with high hydrolytic activity can be prepared by entrapping the fungal cells into calcium alginate gels. When the immobilized cells were incubated in a reaction mixture containing 350g/l DL-pantolactone for 21h at 30゚C under the conditions of automatic pH control (pH 6.8-7.2), 90-95% of the D-pantolactone was hydrolyzed (optical purity, 90-97% e.e.). After repeated reactions for 180 times (i.e., 180 days), the immobilized mycelia retained more than 90% of their initial activity. The enzymatic resolution process of racemic pantolactone can skip several tedious steps which are necessary in the conventional chemical resolution process, and this is a considerable practical advantage.

Report

(3 results)
  • 1997 Annual Research Report   Final Research Report Summary
  • 1996 Annual Research Report
  • Research Products

    (30 results)

All Other

All Publications (30 results)

  • [Publications] M.Kataoka et al.: "Optical resolution of racemic pantoic acid through microbial stereoselective lactonization in two-phase system." Enzyme Microb.Technol.19. 307-310 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] S.Shimizu & M.Kataoka: "Structure,function,and application of microbial lactonases." Chimia. 50. 409-410 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] M.Kataoka et al.: "Crystallization and preliminary X-ray diffraction study of aldehyde reductase from a red yeast,Sporobolomyces salmonicolor." Acta Cryst.D52. 405-406 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] M.Kataoka et al.: "Purification and characterization of L-allo-threonine aldolase from Aeromonas jandaei DK-39." FEMS Microbiol.Lett.151. 245-248 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] M.Kataoka et al.: "Isolation and characterization of D-threonine aldolase,a pyridoxal-5'-phosphate-dependent enzynme from Arthrobacter sp." Eur.J.Biochem.245. 385-393 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] M.Kataoka et al.: "Enzymatic production of ethyl (R) -4-chloro-3-hydroxybuttanoate : Asymmetric reduction of ethyl 4-chloro-3-oxobutanoate." Appl.Microbiol.Biotechnol.48. 699-703 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] S.Shimizu & M.Kataoka: "Enzyme Engineering XIII" New York Academy of Sciences, 9 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] S.Shimizu et al.: "Advances in Biochemical Engineering/Biotechnology,vol.58" Springer-Verlag,Berlin, 42 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] M.Kataoka et al: "Optical resolution of racemic pantoic acid through microbial stereoselective lactonization in two-phase system." Enzyme Microb.Technol.19. 307-310 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] S.Shimizu & M.Kataoka: "Structure, function, and application of microbial lactonases." Chimia. 50. 409-410 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] M.Kataoka et al.: "Crystallization and preliminary X-ray diffraction study of aldehyde reductase from a red yeast, Sporobolomyces salmonicolor." Acta Cryst.D52. 405-406 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] M.Kataoka et al.: "Purification and characterization of L-allo-threonine aldolase from Aeromonas jandaei DK-39." FEMS Microbil.Lett.151. 245-248 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] M.Kataoka et al.: "Isolation and characterization of D-threonine aldolase, apyridoxal-5'-phosphate-dependent enzyme from Arthrobacter sp." Eur.J.Biochem. 245. 385-393 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] M.Kataoka et al.: "Enzymatic production of ethyl (R)-4-chloro-3-hydroxybutanoate : Asymmetric reduction of ethyl 4-chloro-3-oxobutanoate." Appl.Microbiol.Biotechnol.48. 699-703 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] S.Shimizu & M.Kataoka: Enzyme Engineering XIII.New York Academy of Sciences, (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] S.Shimizu et al.: Advabces in Biochemical Engineering/Biotechnology, vol.58. Springer-Verlag, (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] M.Kataoka et al.: "Purification and characterization of L-allo-threonine aldolase from Aeromonas jandaei DK-39." FEMS Microbiol.Lett.151. 245-248 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] M.Kataoka etr al.: "Isolation and characterization of D-threonine aldolase from Arthrobacter sp.DK-38." Eur.J.Biochem.248. 385-393 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] M.Kataoka et al.: "Enzymatic production of ethyl (R)-4-chloro-3-hydroxybutanoate : Asymmetric of reduction of ethyl 4-chloro-3-oxobutanoate." Appl.Microbiol.Biotechnol.48(6). 699-703 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] M.Kobayashi et al.: "Identification of active sites in amidase : Evolutionary relationship between amide bond- and peptide bond-cleaving enzymes." Proc.Natl.Acad.Sci.USA. 94(22). 11986-11991 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] J.Ogawa et al.: "Imidase,a dihydropyrimidinase-like enzyme involved in the metabolism of cyclic imides." Eur.J.Biochem.243. 322-327 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] J.-Q.Liu et al.: "L-allo-Threonine aldolase from Aeromonas jandaei-DK-39 : Gene cloning,nucleotide sequencing,and identification." J.Bacteriol.179(11). 3555-3560 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] S.Shimizu et al.: "Advances in Biochemical Engineering/ Biotechnology,vol.58" Spriger-Verlag,Berlin, 42 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 清水 昌: "高純度化技術大系" フジ・システム、東京, 11 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Himuzu,S.and M.Kataoka: "Optical resolution of pantolactone by a novel fungal enzyme,lactonohydrolase" Annals of the New York Academy of Sciences. 799. 650-658 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Kataoka,M.et al.: "Optical resolution of racemic pantoic acid through microbial stereoselective lactonization in an organic solvent/water two-phase system" Enzyme Microb.Technol.19(9). 307-310 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Shimizu,S.and M.Kataoka: "Structure,function,and application of microbial lactonases" CHIMIA. 50(9). 409-410 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Kataoka,et al.: "Crystallization and preliminary X-ray diffraction study of aldehyde reductase from a red yeast,Sporobolomyces salmonicolor" Acta Cryst.D52. 405-406 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Kobayashi,M.et al.: "Hyperinduction of nitrile hydrtase acting on indole-e-acetonitrile in Agrobacterium tumefaciens" Appl.Microbiol.Biotechnol.45. 176-181 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Ogawa,J.et al.: "Novel metabolic transformation pathway for cyclic imides in Blastobacter sp.strain A17p-4" Appl.Environ.Microbiol.62(10). 3814-3817 (1996)

    • Related Report
      1996 Annual Research Report

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Published: 1996-04-01   Modified: 2016-04-21  

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