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Syntheses of Umami Peptides with Immobilized Papain in Water-Immiscible Organic Solvent Systems

Research Project

Project/Area Number 01560151
Research Category

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

Allocation TypeSingle-year Grants
Research Field 製造化学・食品
Research InstitutionOkayama University

Principal Investigator

NAKANISHI Kazuhiro  Okayama University, Dept. of Biotechnology, Professor, 工学部, 教授 (90026584)

Co-Investigator(Kenkyū-buntansha) TANAKA Takaaki  Okayama University, Dept. of Biotechnology, Instructor, 工学部, 助手 (00217043)
Project Period (FY) 1989 – 1990
Project Status Completed (Fiscal Year 1990)
Budget Amount *help
¥2,200,000 (Direct Cost: ¥2,200,000)
Fiscal Year 1990: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1989: ¥1,600,000 (Direct Cost: ¥1,600,000)
KeywordsImmobilized Enzyme / Papain / Umami-peptide / Dipeptides / Ceramic Support / Enzymatic Synthesis / Reaction in Organic Solvent / ペプチド合成 / グルタミン酸 / アスパラギン酸
Research Abstract

Dipeptides such as L-glutamic acid dimer and L-glutamic acid dimer are known as a substance posessing umami (brothy) taste and a bitter taste masking effect. In this study, we attempted to synthesize precursors of four peptides, i. e., GluGlu, GluAsp, AspGlu, and AspAsp with an immobilized papain in organic solvent systems. As an acid component of a substrate, N-(benzyloxycarbonyl)-L-glutamic acid and N-(benzyloxycarbonyl)-L-aspartic acid, and as an amine component L-glutanic acid diethyl ester and L-aspartic acid diethyl ester were used. In most cases, we focussed on the synthesis of N-(benzyloxycarbonyl)-L-glutamyl-L-glutamic acid diethyl ester (Z-GluGlu(OEt)_2) at 30 ^゚C.
The results obtained are Summarized as follows :
1) The synthetic reaction did not take place in buffer solution.
2) In the aqueous-organic biphasic reaction systems with ethyl acetate as an organic solvent, the maximum yield of Z-GluGlu (OEt) _2 reached about 70%.
3) The enzyme was immobilized onto various porous supp … More orts. The enzyme was first adsorbed onto the support and then cross-linked with glutaraldehyde. The highest activity was obtained when the enzyme was adsorbed onto porous ceramic support (SM10-C1, Nippon Gaishi K. K.).
4) The activity of immobilized enzyme depended strongly on the water content in an outer organic solvent. The highest activity was obtained at a water content of 2.5% with the enzyme immobilized onto SM10-C1.
5) L-Glutamic acid diethyl ester, an amine component of the substrate was non-enzymatically coverted to L-pyroglutamic acid diethyl ester. To reduce the effect of non-enzymatic reaction, the increase of the concentration of the immobilized enzyme was found most effective. With 100 mM Z-Glu and 200 mM Glu (OEt) _2, and immobilized enzyme concentration of 8%, the yield became higher than 90%.
6) The other three dipeptides precursors were also obtained with quite a high yield under the same reaction conditions as shown in (5).
7) The products were identified by analyzing with nuclear magnetic resonance, mass spectrum, and infrared adsorption spectrum. Less

Report

(3 results)
  • 1990 Annual Research Report   Final Research Report Summary
  • 1989 Annual Research Report
  • Research Products

    (12 results)

All Other

All Publications (12 results)

  • [Publications] 中西 一弘: "水ー有機溶媒二相系反応を利用したオリゴペプチドの合成" バイオサイエンスとインダストリ-. 47. 19-26 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Kazuhiro Nakanishi,Akira Takeuchi,Ryuichi Matsuno: "Longーterm continuous synthesis of aspartame precursor in a column reactor with an immobilized thermolysin." Appl.Microbiol.Biotechnol.32. 633-636 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Kazuhiro Nakanishi,Ryuichi Matsuno: "Bioreactors in organic solvent for peptide synthesis." Proc.ApBio ChEC'90. 70-73 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] T.Tanaka,K.Tomita,K.Nakanishi: "Enzymatic synthesis of Lーglutamic acid precursor with immobilized papain in an organic solvent." Chemistry Express. 5. 525-528 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Kazuhiro Nakanishi,Ryuichi Matsuno: "Continuous peptide synthesis in a waterーimmisible organic solvent with an immobilized enzyme." Enzyme Engineering. 10.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Kazuhiro Nakanishi: "Enzymatic synthesis of oligopeptides in aqueous-organic biphasic systems" Bioscience & Industry. 47. 19-26 (1989)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Kazuhiro Nakanishi, Akira Takeuchi, and Ryuichi Matsuno: "Long-term continuous synthesis of aspartame precursor in a column reactor with an immobilized thermolysin." Appl. Microbiol. Biotechnol.32. 633-636 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Kazuhiro Nakanishi and Ryuichi Matsuno: "Bioreactors in organic solvent for peptide synthesis." Proc. APBioChEC '90. 70-73 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Takaaki Tanaka, Kenji Tomita and Kazuhiro Nakanishi: "Enzymatic synthesis of L-glutamic acid precursor with immobilized papain in an organic solvent" Chemistry Express. 5. 525-528 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Kazuhiro Nakanishi and Ryuichi Matsuno: "Continuous peptide synthesis in a water-immersible organic solvent with an immobilized enzyme" Proc. 10th Enzyme engineering conference.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Takaaki TANAKA: "Enzymatic Synthesis of LーGlutamic Acid Dimer Precursor with Immobilized Papain in an Organic solvent" Chemistry Express. 5. 525-528 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] 中西一弘: "水ー有機溶媒=相系を利用したオリゴペプチドの合成" バイオサイエンスとインダストリ-. 47. 19-26 (1989)

    • Related Report
      1989 Annual Research Report

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Published: 1989-04-01   Modified: 2016-04-21  

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