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Enzymatic transformation of -chloroalanine into useful amino acids

Research Project

Project/Area Number 61560117
Research Category

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

Allocation TypeSingle-year Grants
Research Field 000130000136000246
Research InstitutionKyoto University

Principal Investigator

NAGASAWA Toru  Kyoto University, Faculty of Agriculture, Assistant, 農学部, 助手 (60115904)

Co-Investigator(Kenkyū-buntansha) SHIMIZU Sakayu  Kyoto University, Faculty of Agriculture, Assistant, 農学部, 助手 (70093250)
IZUMI Yoshikazu  Kyoto University, Faculty of Agriculture, Associate Professor, 農学部, 助教授 (40026555)
Project Period (FY) 1986 – 1987
Project Status Completed (Fiscal Year 1987)
Budget Amount *help
¥1,900,000 (Direct Cost: ¥1,900,000)
Fiscal Year 1987: ¥300,000 (Direct Cost: ¥300,000)
Fiscal Year 1986: ¥1,600,000 (Direct Cost: ¥1,600,000)
Keywords-chloroalanine / O-acetylserine sulfhydrylase / -chloroalanine dehydrochlorinase / L-cysteine / D-cysteine / 半合成セファロスポリン / 【B_6】酵素 / 酵素的転換 / Bacillus sphaerincus / Pseudomonas putida
Research Abstract

Recent development of chemical synthesis techniques has made it possible to produce <beta>-chloroalanine economically on a large scale. The enzymatic transformation of chemically synthesized <beta>-chloroalanie into useful amino acids was studied. We isolated microorganisms, Bacillus sphaericus L-118 and Pseudomonas putida CR1-1 which are resistant to <beta>-chloro-L-alanine and -chloro-D-alanine, respectively. The formation of O-acetylserine sulfhydrylase of B. sphaericus L-118, was highly enhanced by (beta)-chloro-L-alanine to the medium. The enzyme catalyzes the <beta>-replacement reaction of <beta>-chloroalanine in the presence of sulfide to produce L-cysteine. We optimized the reaction conditions for the enzymatic production of L-cysteine. Under the optimum conditions. 70 g of L-cysteine/L of reaction mixture was produced (conversion yield 80%). In the crude cell extract of P. putida CR 1-1, we found the new enzyme, <beta>-chloro-D-alanine dehydrochlorinase which catalyzes the <beta>-replacement reaction of <beta>-chloro-D-alanine in the presence of sulfide to produce D-cysteine. When various thiol compounds were added instead of sulfide, the corresponding Salkyl-D-cysteine was synthesized. We optimized the reaction conditions to produce D-cysteine. Under the optimal condition, 22.6 g of D-cysteine/L of reaction mixture was produced (conversion yield 100%). D-Cysteine and its derivatives are useful for the production of the semi-synthetic cephalosporin antibiotics.

Report

(2 results)
  • 1987 Final Research Report Summary
  • 1986 Annual Research Report
  • Research Products

    (20 results)

All Other

All Publications (20 results)

  • [Publications] Toru Nagasawa: Journal of Biological Chemistry. 257. 13749-13756 (1982)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Toru Nagasawa: Journal of Biotechnology. 2. 367-377 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Toru Nagasawa: Applied Biochemistry Biotechnology. 13. 147-165 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] 長沢透: 日本農芸化学会誌. 61. 165-174 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] G.C.Dhillon: Microbial Technology. 9. 277-280 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Toru Nagasawa: Achives of Microbiology. in press.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Toru Nagasawa: "Biotechnolgy of amino acid production" Elsevier(Amsterdam-Oxford-New York-Tokyo), 340 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Toru Nagasawa: "Sulfur and Sulfur Amino Acids(Methods in Enzymology vol.143)" Academic Press,Inc.(Orlando San Diego New York Austin Boston Sydney Tokyo Toronto), 582 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Toru Nagasawa: "3-Chloroalanine chloride-lyase(deaminating) of Pseudomonas putida CR 1-1" Journal of Biological Chemistry. 257. 13749-13756 (1982)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Toru Nagasawa: "Enzymatic synthesis of L-cysteineby O-acetylserine sulfhydrylase of of 3-chloro-L-alanine resistant Bacillus sphaericus L-118" Journal of Biotechnology. 2. 367-377 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Toru Nagasawa: "Enzymatic transformation of 3-chloroalanine into useful amino acids" Applied Biochemistry and Biotechnology. 13. 147-165 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] G.S. Dhillon: "Enzyme Microbial Technology" Microbial process for L-cysteine production. 9. 277-280 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Toru Nagasawa: "Physiological comparison of D-cysteine desulfhydrase of Escherichia coli with 3-chloro-D-alanine dehydrochlorinase of Pseudomonas putida CR 1-1" Archives of Microbiology.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Toru Nagasawa: Biotechnology of amino acid production. Elsevier, 340 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Toru Nagasawa: Journal of Biotechnology. 2. 365-377 (1985)

    • Related Report
      1986 Annual Research Report
  • [Publications] Toru Nagasawa: European Journal of Biochemistry. 153. 541-551 (1985)

    • Related Report
      1986 Annual Research Report
  • [Publications] Toru Nagasawa: Appl.Biochem.Biotechnol.13. 145-165 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] 長沢透: 日本農芸化学会誌. 161. 165-174 (1987)

    • Related Report
      1986 Annual Research Report
  • [Publications] Toru Nagasawa: "Biotechnology of Amino Acid Production Progress in Industrial Microbiology" Elsevier Science Press, 7 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] Toru Nagasawa: "Methods in Enzymology" Academic Press, (1987)

    • Related Report
      1986 Annual Research Report

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

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