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Regio- and Stereoselective Reduction of Substituted 1.3-Dicarbonyl Compounds by Use of Bakers' Yeast

Research Project

Project/Area Number 04650775
Research Category

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

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionOkayama University

Principal Investigator

UTAKA Masanori  Okayama University, Department of Engineering, Professor, 工学部, 教授 (30033153)

Co-Investigator(Kenkyū-buntansha) SAKAI Takashi  Okayama University, Department of Engineering, Associate Professor, 工学部, 助教授 (00170556)
Project Period (FY) 1992 – 1993
Project Status Completed (Fiscal Year 1993)
Budget Amount *help
¥1,900,000 (Direct Cost: ¥1,900,000)
Fiscal Year 1993: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1992: ¥1,400,000 (Direct Cost: ¥1,400,000)
Keywordsoptically active gamma -substituted beta -hydroxy ketones / Bakers' yeast asymmetric reduction / trifunctional chiral synthons / optically active alpha -acetoxy alcohols / optically active chlorohydrins / 光学活性1,2-ジオール誘導体 / 1,3-ジケトン / α-アセトキシケトン / 1-アセトキシ-2,4-アルカンジオン / 不斉還元 / パン酵母還元 / 1.3-ジケトン / 位置選択的還元 / キラルシントン
Research Abstract

1. Effects of Additives of the Bakers' Yeast Reduction of 1-Chloro-2,4-alkanediones---The % ee values of reduction products were found to be enhanced by addition of SrCl_2 in 2 mol/L to the aqueous reaction solution. Other metal chlorides also exhibited similar effects, though not so large. The effects can be attributed to selective activation or inhibition of additives toward plural reducing enzymes.
2. Bakers' Yeast Reduction of 1-Acetoxy-2,4-alkanediones ---The reduction produced (S)-1-acetoxy-2-hydroxy-4-alkanones in 40 - 90% ee, as compared with the reduction of 1-acetoxy-2-alkanones with 95 - >99% ee. The somewhat diminished % ee values can be attributed to the presence of an oxo functional group at C-4. The oxo group effectively suppressed the hydrolysis of the acetoxy group, which occurred for 1-acetoxy-2-alkanones and produces 1,2-diols as by-product. The optically active trifunctional products are useful as chiral synthons.
3. Highly Efficient Asymmetric Reduction by Use of Bakers' Yeast Cell-Free Extract---The cell-free extract was found to reduce 1-acetoxy-2-alkanones to 1-acetoxy-2-alkanols in 59 - 88% yield and 95 - >99% ee by use of a catalytic amount of NADPH with glucose as hydride source and without addition of any enzyme for the cofactor regeneration. This method is expected to be applicable to 1-chloro- and 1-acetoxy-2,4-alkanediones.

Report

(3 results)
  • 1993 Annual Research Report   Final Research Report Summary
  • 1992 Annual Research Report
  • Research Products

    (7 results)

All Other

All Publications (7 results)

  • [Publications] Kohji Ishihara,Takashi Sakai,Masanori Utaka: "Highly Efficient Enzymatic Asymmetric Reduction by Use of Regenerating NADPH in Bakers' Yeast Cell-Free Extract" Tetrahedron Letters. 35. (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Masanori Utaka,Toshiyuki Mizumoto,Sadao Tsuboi: "Regio- and Enantioselective Reduction of 1-Acetoxy-2,4-alkanediones by Use of Fermenting Bakers' Yeast" Tetrahedron Letters. 35(to be published). (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Kohji Ishihara,Nobuyoshi Nakajima,Sadao Tsuboi,Masanori Utaka: "Purification and Characterization of α-Acetoxy Ketone Reductase from Bakers' Yeast(Saccharomyces cerevisiae)" Journal of Biochemistry. (to be published). (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Kohji Ishihara, Takashi Sakai, Sadao Tsuboi, Masanori Utaka: "Highly Efficient Enzymatic Asymmetric Reduction by use of Regenerating NADPH in Bakers' Yeast Cell-Free Extract" Tetrahedron Letters. 35 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Masanori Utaka, Toshiyuki Mizumoto, Sadao Tsuboi: "Regio- and Enantioselective Reduction of 1-Ace-toxy-2,4-alkanediones by Use of Fermenting Baker's Yeast" Tetrahedron Letters. (to be published). 35 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Kohji Ishihara, Nobuyoshi Nakajima, Sadao Tsuboi, Masanori Utaka: "Purification and Characterization of alpha -Acetoxy Ketone Reductase from Bakers' Yeast (Saccharomyces cerevisiae)" Journal of Biochemistry. (to be published). (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Kohji Ishihara: "Highly Efficient Enzymatic Asymmetric Reduction by Use of Regenerating NADPH in Bakers' Yeast Cell-Free---" Tetrahedron Letters. 35. (1994)

    • Related Report
      1993 Annual Research Report

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Published: 1992-04-01   Modified: 2016-04-21  

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