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1988 Fiscal Year Final Research Report Summary

Enzymatic processes for the production of D-pantoyl lactone and related optically active hydroxylated compounds

Research Project

Project/Area Number 62560102
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
Research Field 発酵・醸造
Research InstitutionKyoto University

Principal Investigator

SHIMIZU Sakayu  Kyoto University, 農学部, 助手 (70093250)

Co-Investigator(Kenkyū-buntansha) NAGASAWA Toru  Kyoto University, 農学部, 助手 (60115904)
IZUMI Yoshikazu  Kyoto University, 農学部, 助教授 (40026555)
Project Period (FY) 1987 – 1988
KeywordsStereoselective reaction / D(-)-pantoyl lactone / Nocardia asteroids / Candida parapsilosis / Candida parapsilosis / Rhodotorula minuta / Nocardia asteroides
Research Abstract

The efficient enzymatic conversion of ketopantoyl lactone to D-(-)-pantoyl lactone was found to take place on incubation with washed cells of Candida parapsilosis IFO 0708 or Rhodotorula minuta IFO 0920. They showed high conversion activity when grown with 5% corn steep liquor and 5% glucose, sucrose,maltose or glycerol.Under suitable reaction conditions the amounts of D-(-)-pantoyl lactone reached 49.5g/l(94.4%e.e; molar yield,99%) and 89.9g/l(80.4%e.e; molar yield,99%)with cells of R.minuta and C.parapsilosis,respectively.
A novel enzymatic process for the synthesis of D(-)-pantoyl lactone from a racemic mixture of pantoyllactone was also developed.The process involves the stereospecific oxidation of the L(+)-isomer of pantoyl lactoneto ketopantoyl lactone followed by its asymmetric reduction to the D(-)-isomer. The oxidation is carried out with cells of Nocardia asteroides AKU 2103 as the catalyst, which convert only the L(+)-isomer of pantoyl lactone to keto-pantoyl lactone without any modification of the remaining D(-)-isomer.With 80gl^<-1> DL-pantoyl lactone as the substrate,>90%of the added L(+)-isomer was converted to ketopantoyl lactone under the optimum reaction conditions. The ketopantoyl lactone that accumulated in the reaction mixture was almost specifically converted to the D(-)-isomer of pantoyl lactone on incubation with cells of Candida parapsilosis IFO 0784. Scince this process is simple and requires no reracemization step, which is necessary for conventional chemical resolution, it is highly advantageous for the practical synthesis of D(-)-pantoyl lactone.

  • Research Products

    (11 results)

All Other

All Publications (11 results)

  • [Publications] Sakayu Shimizu.: Applied and Environmental Microbiology. 53. 519-522 (1987)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Sakayu Shimizu: Enzyme Microbial Technology. 9. 411-416 (1987)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Hiroyuki Hata.: Agricultural and Biological Chemistry. 51. 3011-3016 (1987)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Sakayu Shimizu.: Agricultural and Biological Chemistry. 51. 289-290 (1987)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Sakayu Shimizu.: European Journal of Biochemistry. 174. 37-44 (1988)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Sakayu Shimizu.: Journal of Biological Chemistry. 263. 12077-12084 (1988)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Sakayu Shimizu: "One-Step Microbial Conversion of Racemic Mixture of Pantoyl Lactone to Optically Active D-(-)-Pantoyl Lactone" Applied and Environmental Microbiology. 53. 519-522 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Sakayu Shimizu: "Stereoselective enzymatic oxidation and reduction system for the production of D-(-)-pantoyl lactone from a racemic mixture of pantoyl lactone" Enzyme Microbial Technology. 9. 411-416 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hiroyuki Hata: "Enzymatic Production of D-(-)-Pantoyl Lactone from Ketopantoyl Lactone" Agricultural and Biological Chemistry. 51. 3011-3016 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Sakayu Shimizu: "Novel Chemoenzymatic Synthesis of D-(-)-Pantoyl Lactone" Agricultural and Biological Chemistry. 51. 289-290 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Sakayu Shimizu: "A novel fungal enzyme, NADPH-dependent carbonyl reductase, showing high specificity to conjugated polyketones; Purification and characterization" European Journal of Biochemistry. 174. 37-44 (1988)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 1990-03-20  

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