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Ultra-highly effective utilization of lipid resources-Enzymatic syntheses of structured lipids-

Research Project

Project/Area Number 12839004
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field 生物資源の変換と展開
Research InstitutionNagoya University

Principal Investigator

YAMANE Tsuneo  Nagoya University, Graduate School of Bio-& Agro-Sciences, Professor, 大学院・生命農学研究科, 教授 (70026102)

Co-Investigator(Kenkyū-buntansha) NAKANO Hideo  Nagoya University, Graduate School of Bio-& Agro-Sciences, Associate Professor, 大学院・生命農学研究科, 助教授 (00237348)
Project Period (FY) 2000 – 2002
Project Status Completed (Fiscal Year 2002)
Budget Amount *help
¥3,100,000 (Direct Cost: ¥3,100,000)
Fiscal Year 2002: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 2001: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 2000: ¥1,900,000 (Direct Cost: ¥1,900,000)
Keywordsstructured lipid / chiral lipid / lipase / phospholipase D / polyunsaturated fattyacid acid / transesterifiation / diacylglycerol / phosphatidylserine / DHA / EPA
Research Abstract

1. As a prerequisite to this project, we succeeded in separation and determination of symmetrical structured triacylglycerol, ABA (where A=n-octanoic acid, B=a polyunsaturated fatty acid, PUFA), and asymmetrical ones, AAB (and/or BAA) by use of a combination of silver ion HPLC and chiral HPLC. We also succeeded in the separation and determination of chiral diacylglycerols, AA (OH) and (OH) AA.
2. Symmetrical structured triacylglycerol, ABA, was able to be synthesized very effectively by a two-step method which was composed of ethanolysis of bonito oil with immobilized Candida antarctica lipase, and then esterification of the resulting monoacylglycerol, (OH) (PUFA) (OH) with immobilized Rizomucor miehei lipase.
3. From egg yolk lecithin containing 13% docosahexaenoic acid and excessive L-serine, phosphatidylserine was able to be synthesized successfully by the transphosphatidylation action of phospholipase D.

Report

(4 results)
  • 2002 Annual Research Report   Final Research Report Summary
  • 2001 Annual Research Report
  • 2000 Annual Research Report
  • Research Products

    (31 results)

All Other

All Publications (31 results)

  • [Publications] R.Irimescu et al.: "Two-Step Enzymatic Synthesis of Docosahexaenoic Acid-rich Symmetrically Structured Triacylglycerols via 2 -Monoacylglycerols"Journal of the American Oil Chemists' Society. 78・7. 743-748 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] R.Irimescu et al.: "Utilization of Reaction Medium-Dependent Regiospecificity of Candida antarctica Lipase (Novozym 435)for the Synthesis of 1,3-Dicapryloyl-2-docosahexaenoyl (or eicosapentaenoyl) Glycerol"Journal of the American Oil Chemists' Society. 78・3. 285-289 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] R.Irimescu et al.: "Comparison of Acyl Donors for Lipase-Catalyzed Production of 1,3-Dicapryloy1-2-eicosapentaenoylglycerol"Journal of the American Oil Chemists' Society. 78・1. 65-70 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Yugo Iwasaki et al.: "Optical resolution of asymmetric triacylglycerols by chiral-phase high-performance liquid chromatography"Journal of Chromatography A. 905・1. 111-118 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] R.Irimescu et al.: "Enzymatic Synthesis of 1,3-Dicapryloyl-2-eicosapentaenoylglycerol"Journal of the American Oil Chemists' Society. 77・5. 501-506 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Yugo Iwasaki, Tsuneo Yamane: "Enzymatic synthesis of structured lipids"Journal of Molecular Catalysis B : Enzymatic. 10・9. 129-140 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] R.Irimescu et al: "Enzymatic synthesis of 1,3-dicapry-loyl-2-eicosapentaenoylglycerol"Journal of the American Oil Chemists' Society. 77. 501-506 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] R.Irimescu et al: "Comparison of acyl donners for lipase-catalyzed production of 1,3-dicapryoyl-2-eicosapentaenoyl-glycerol"Journal of the American Oil Chemists' Society. 78. 65-70 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] R.Irimescu et al: "Utilization of reaction medium-dependent regiospecificity of Candida antarctica lipase (Novozym 435) for the synthesis of 1,3-dicapryoyl-2-docosahexaenoyl (or eicosapentaenoyl) glycerol"Journal of the American Oil Chemists' Society. 78. 285-289 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] R.Irimescu et al: "Two-step enzymatic synthesis of docosahexaenoic acid-rich symmetrically structuted triacyl-glycerols via 2-monoglycerols"Journal of the American Oil Chemists' Society. 78. 743-748 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Y.Iwasaki et al: "Optical resolution of asymmetric triacylglycerols by chiral-phase high-performance liquid chromatography"Journal of Chromatography A. 905. 111-118 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Yugo Iwasaki and Tsuneo Yamane: "Enzymatic synthesis of structured lipids"Journal of Molecular catalysis B : Enzymatic. 10. 129-140 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Tsuneo Yamane and Yugo Iwasaki: "Functional Lipids and Biotechnology"Biosrience and Industry. 58. 837-844 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Yugo Iwasaki and Tsuneo Yamane: "Enzymatic Syntheses of Structured Lipids"Oleoscience. 1. 825-833 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Tsuneo Yamane, ed.by Uwe T.Bomscheuer: "Lipase-catalyzed Synthesis of Structured Triacylglycerols Containing Polyunsaturated Fatty Acids. Monitoring of the Reaction and Increasing the Yield, "Enzymes in Lipid Modification", Chapter 9"Wiley-VCH Verlag GmbH. 148-169 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Tsuneo Yamane, ed.by J.Vulfson, P.J.Halling, and H.L.Holland: "Solvent-free Biotransformations of Lipids, "Enzymes in Nonaqueous Solvents", Chapter 38"The Humana Press Inc.. 509-516 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Yugo Iwasaki and Tsuneo Yamane, ed.by T.M.Kuo and H.W.Gardner: "Phospholipases in Enzyme Engineering of phospholipids for Food, Cosmetics, and Medical Applications, "Lipid Biotechnology", Chapter 20"Marcel Dekker, Inc.. 417-431 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Y.Iwasaki, T.Yamane: "Phospholipases in Enzyme Engineering of phospholipids for Food. Cosmetics, and medical Applications in "Lipid Biotechnology"chap 20"Marcel Dekker. Inc., New York. 716 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Roxana Irimescu: "Enzymatic synthesis of 1,3-dicapryloy1-2-eicosapentaenoylglycerol"J. Am. Oil Chem. Soc.. 77・5. 501-506 (2000)

    • Related Report
      2001 Annual Research Report
  • [Publications] Yugo Iwasaki: "Enzymatic synthesis of structured lipids"Journal of Molecular Catalysis B : Enzymatic. 10・9. 129-140 (2000)

    • Related Report
      2001 Annual Research Report
  • [Publications] Yugo Iwasaki: "Optical resolution of asymmetric triacylglycerols by chiral-phase high performance liquid chromatography"J. Chromatography A. 905・1. 111-118 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Roxana Irimescu: "Comparison of acyl donors for lipase-catalyzed production of 1,3-dicapryloy1-2-eicosapentaenoylglycerol"J. Am. Oil Chem. Soc.. 78・1. 65-70 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Roxana Irimescu: "Utilization of reaction medium-dependent regiospecificity of Candida antarctica lipase for the synthesis of 1,3-dicapryloy1-2-DHA-glycerol"J. Am. Oil Chem. Soc.. 78・3. 285-289 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Roxana Irimescu: "Two-step enzymatic synthesis of docosahexaenoic acid-rich symmetrically structured triacylglycerols via 2-monoacylglycerols"J. Am. Oil Chem. Soc.. 78・7. 743-748 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] T. Yamane: ""Enzymes in Lipid Modification" ed. By U. T. Bornscheuer, Chap. 9(148-169)"Wiley-VCH. 21 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] T.Yamane et al: "Enzymatic Synthesis of 1,3-Dicapryloyl-2-eicosapentaenoylglycerol"J.Am.Oil Chem.Soc.. 77・5. 501-506 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Yamane et al: "Enzymatic synthesis of structured lipids"Journal of Molecular Catalysis B : Enzymatic. 10・9. 129-140 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Yamane et al: "Optical resolution of asymmetric triacylglycerols by chiral-phase high-performance liquid chromatography"Journal of Chromatography A. 905. 111-118 (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Yamane et al: "Comparison of acyl doners for lipase-catalyzed production of 1,3-dicapryloyl-2-eicosapentaenolglycerol"J.Am.Oil Chem.Soc.. 78・1. 65-70 (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Yamane et al: "Utilization of reaction medium-dependent regiospecificity of Candida antarctica lipase for the synthesis of 1,3-dicapryloyl-2-DHA-glycerol"J.Am.Oil Chem.Soc.. (印刷中). (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Yamane: ""Enzyme in Lipid Modification" ed.by U.T.Bornscheuer, Chap.9(pp.148-169)"Wiley-VCH. 21 (2001)

    • Related Report
      2000 Annual Research Report

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Published: 2000-04-01   Modified: 2016-04-21  

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