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Solvent Engineering on Enzymatic Synthesis of Edible Surfactants

Research Project

Project/Area Number 06453175
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field 食品科学・栄養科学
Research InstitutionKYOTO UNIVERSITY

Principal Investigator

MATSUNO Ryuichi  Kyoto University, Department of Food Science and Technology, Professor, 農学部, 教授 (30032931)

Co-Investigator(Kenkyū-buntansha) KIMURA Yukitaka  Kyoto University, Department of Food Science and Technology, Instructor, 農学部, 助手 (70211878)
ADACHI Shuji  Kyoto University, Department of Food Science and Technology, Associate Professor, 農学部, 助教授 (90115783)
Project Period (FY) 1994 – 1996
Project Status Completed (Fiscal Year 1996)
Budget Amount *help
¥7,300,000 (Direct Cost: ¥7,300,000)
Fiscal Year 1996: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1995: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1994: ¥6,200,000 (Direct Cost: ¥6,200,000)
KeywordsSolvent Engineering / Surfactant / Condensation / Biocatalyst / beta-Glucosidase / Lipase / 可食性界面活性剤 / アルキルグルコシド / 吸着等温線 / エリスリトール / アスコルビン酸 / 酵素合成 / アシル化糖 / 縮合 / 酵素工学
Research Abstract

Enzymatic synthesis of edible surfactants from hydrophilic and hydrophobic ingredients in food was invesigated. In the first stage of this investigation, b-glucosidase-catalyzed synthesis of alkyl glucosides was made to understand phenomena occuring in such synthetic reaction, although the glucosides are not edible but have a wide range of industrial use. We proposed the equations to predict the yields of desired product and by-products in a conventional aqueous-organic biphasic system, where one of substrates, alcohol, itself was an organic phase. It was found that the equilibrium constant for condensation of glucose and alcohol was independent of the alkyl chain length of alcohol. We proposed a novel reaction system where solid enzyme and glucose were added to alcohol saturated with a buffer. The equilibrium yield of alkyl glucoside in the proposed system was much higher than that in the conventional two-phase system. High stability of the enzyme in the system allowed its reuse in subsequent condensation. It was also found in the system that both of (R) -and (S) -isomers of secondary alcohol could be condensed with glucose by the enzyme to give corresponding glucosides in high yield. A packing material for effective liquid-chromatographic separation of alkyl glucoside and alcohol was found out. A model was proposed to explain the dependence of elution times of solutes on the composition of eluent. Simple methods were proposed for estimation of adsorption isotherm of a solute on an adesorbent from only a pulse response curve ofthe solute. Acylation of erythritol and ascorbic acid by immobilized lipase was also examined. The acylation proceeded stereoselectively in acetonitril with extremely low content of water. The products were identified to be desired products by NMR analysis.

Report

(4 results)
  • 1996 Annual Research Report   Final Research Report Summary
  • 1995 Annual Research Report
  • 1994 Annual Research Report
  • Research Products

    (11 results)

All Other

All Publications (11 results)

  • [Publications] Shuji Adachi: "Separation of Alkyl-β-D-glucosides and n-Alcohols by Using a Porous Trimethylolpropane Trimethacrylate Homopolymer Gel." Bioscience, Biotechnology and Biochemistry. 58 (9). 1558-1563 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Chaiya Panintrarux: "Equilibrium Yield of η-Alkyl-β-D-glucoside through Condensation of Glucose and η-Alcohol by β-Glucosidase in a Biphasic System." Enzyme and Microbial Technology. 17 (1). 32-40 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Chaiya Panintrarux: "η-Octyl β-D-Glucoside Synthesis through β-Glicosidase Catalyzed Condensation of Glucose and η-Octanol in a Heterogeneous System with High Glucose Concentration" Journal of Molecular Catalysis B : Enzymatic. 1 (2). 165-172 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] S.Adachi, C.Panintrarux, Y.Araki, Y.Kimura, and R.Matsuno: "Separation of Alkyl-beta-D-glucosides and n-Alcohols by Using a Porous Trimethylolpropane Trimethacrylate Homopolymer Gel" Biosci.Biotech.Biochem.58(9). 1558-1563 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] C.Panintrarux, S.Adachi, Y.Araki, Y.Kimura, and R.Matsuno: "Equilibrium Yield of n-Alkyl-beta-D-glucoside through Condensation of Glucose and n-Alcohol by beta-Glucosidase in a Biphasic System" Enzyme Microb.Technol.17(1). 32-40 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] C.Panintrarux, S.Adachi, and R.Matsuno: "n-Octyl beta-D-Glucoside synthesis through beta-Glucosidase Catalyzed Condensation of Glucose and n-Octanol in a Heterogeneous System with High Glucose Concentration" J.Mol.Catal.B,Enzymatic. 1(2). 165-172 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Chaiya Panintrarux: "n-Octyl β-D-glucoside synthesis through β-glucosidase catalyzed condensation of glucose and n-octanol in a heterogeneous system with high glucose concentration." Journal of Molecular Catalysis B : Enzymatic. 1(2). 367-372 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Chaiya Panintrarux: "n-Octy1 β-glucoside synthesis through β-glucosidase catalyzed condensation of glucose and n-octanol in a heterogeneous system with high glucose concentration" Journal of Molecular Catalysis B: Enzymatic. 14(in press). (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] Shuji Adachi: "Separation of alkyl β-D-glucosides and n-alcohols by using porous trimethylolpropane trimethacrylate homopolymer gel." Bioscience,Biotechnology and Biochemistry. 58. 1558-1563 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Yukitaka Kimura: "Equilibrium study on alkyl-β-D-glucoside synthesis from glucose and alcohol by β-glucosidase" Enzyme Engineering. 12. 312-316 (1995)

    • Related Report
      1994 Annual Research Report
  • [Publications] Chaiya Panintrarux: "Equilibrium yield of n-alkyl-β-D-glucoside through condensation of glucose and n-alcohol by β-glucosidase in a biphasic system" Enzyme and Microbial Technology. 17(印刷中). (1995)

    • Related Report
      1994 Annual Research Report

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Published: 1994-04-01   Modified: 2016-04-21  

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