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The Enantioselective Synthesis of Some Useful Antibiotics based on the Chemicoenzymatic Strategy.

Research Project

Project/Area Number 59430024
Research Category

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

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionFaculty of Pharmaceutical Sciences, University of Tokyo

Principal Investigator

OHNO Masaji  Faculty of Pharmaceutical Sciences, Univ. of Tokyo, Professor, 薬学部, 教授 (00111550)

Project Period (FY) 1984 – 1986
Project Status Completed (Fiscal Year 1986)
Budget Amount *help
¥26,900,000 (Direct Cost: ¥26,900,000)
Fiscal Year 1986: ¥1,500,000 (Direct Cost: ¥1,500,000)
Fiscal Year 1985: ¥4,000,000 (Direct Cost: ¥4,000,000)
Fiscal Year 1984: ¥21,400,000 (Direct Cost: ¥21,400,000)
KeywordsPig liver esterase / Synthesis of antibiotics / Symmetrization-asymmetrization concept / Retrosynthesis / Fortimicine / リゾチシン / 豚肝臓エステラーゼ / 4-シクロヘキセン-1 / 2-シス-ジカルボン酸メチルエステル / カルバペネム / ミルベマイシン / アバメクチン / リゾキシン
Research Abstract

Since 1978, we have begun to synthesize biologically active natural products by a reasonable combination of enzymatic process (pig liver esterase, PLE) and usual organic synthesis and developed a new avenue for natural product synthesis. Our synthetic strategy for obtaining various antibiotics has therefore been designed as follows.
(1) Retrosynthesis is performed to generate, from the target molecule, a symmetric diester in the prochiral or meso form.
(2) The symmetric diester is subjected to asymmetric hydrolysis with pig liver esterase to generate the corresponding chiral half-ester. (enzymatic conversion of <sigma> -symmetry to <C_1> -symmetry)
(3) The chiral half-ester is converted to the target molecule by means of organic synthesis. The total strategy is called "Symmetrization-asymmetrization Concept".
Thus, in addition to various carbapenem antibiotics and nucleosides, fortimicin A and part of rhizoxin were synthesized and the results were presented at various famous international meetings of the world.

Report

(2 results)
  • 1986 Final Research Report Summary
  • 1985 Annual Research Report
  • Research Products

    (7 results)

All Other

All Publications (7 results)

  • [Publications] 大野雅二編著: "酵素機能と精密有機合成" シーエムシー, (1984)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] 大野雅二,大村智編著: "抗生物質研究の最先端" 東京化学同人, (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Masaji Ohno: C. M. C.Enzyme Function and Organic Synthesis, (1984)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Masaji Ohno, Satoru Ohmura: Tokyo Kagaku Dohjin. Recent Advances on Antibiotic Research, (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] IUPAC第5回国際有機合成化学会議. (1985)

    • Related Report
      1985 Annual Research Report
  • [Publications] Tetrahedron Letters. 26. (1985)

    • Related Report
      1985 Annual Research Report
  • [Publications] 有機合成化学協会誌. 44. (1986)

    • Related Report
      1985 Annual Research Report

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Published: 1987-03-31   Modified: 2016-04-21  

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