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Solid Phase Synthesis in Water-Development of Green Chemistry

Research Project

Project/Area Number 14572024
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionKobe Gakuin University

Principal Investigator

KAWASAKI Koichi  Kobe Gakuin University, Faculty of Pharmaceutical Sciences, Professor, 薬学部, 教授 (40068242)

Co-Investigator(Kenkyū-buntansha) MAEDA Mitsuko  Kobe Gakuin University, Faculty of Pharmaceutical Sciences, Senior Assistant, 薬学部, 助手 (90131531)
HOJO Keiko  Kobe Gakuin University, Faculty of Pharmaceutical Sciences, Research Assistant, 薬学部, 実験助手 (20289028)
Project Period (FY) 2002 – 2004
Project Status Completed (Fiscal Year 2004)
Budget Amount *help
¥3,200,000 (Direct Cost: ¥3,200,000)
Fiscal Year 2004: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 2003: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 2002: ¥1,100,000 (Direct Cost: ¥1,100,000)
Keywordssolid phase synthesis / peptide synthesis / green chemistry / Leu-enkephalin / water-soluble protecting group / water / 水中合成 / 2-(4-sulfophenyl)ethoxycarbonyl group / 水中固相合成 / エンケファリン / 水溶性保護アミノ酸 / 水系固相法合成 / 2-[phenyl(methyl)sulfonio]eyhoxycarbonyl基
Research Abstract

Solid phase peptide synthesis (SPPS) is a well-established technique for the facile and rapid preparation of peptides, but it requires large amounts of organic solvents. Since the safe disposal of organic solvents is an important environmental issue, the ability to synthesize peptides in an aqueous medium would be preferable. In order to do so, water-soluble N-protected amino acids are necessary. We have successfully used the water-soluble N-protecting groups, 2-[phenyl(methyl)sulfonio]ethoxycarbonyl (Pms), ethanesulfonylethoxycarbonyl (Esc) and 2-(4-sulfophenylsulfonyl)ethoxycarbonyl (Sps), for the SPPS of Leu-enkephalin amide in water.

Report

(4 results)
  • 2004 Annual Research Report   Final Research Report Summary
  • 2003 Annual Research Report
  • 2002 Annual Research Report
  • Research Products

    (20 results)

All 2005 2004 2003 2002 Other

All Journal Article (17 results) Publications (3 results)

  • [Journal Article] Design of reagents for preparing water-soluble N-protected amino acids.2005

    • Author(s)
      Hojo, K., Maeda, M., Kawasaki, K.
    • Journal Title

      Innovation and Perspectives in Solid Phase Synthesis & Combinatorial Libraries 2004 (Edited by Epton, R.)(Mayflower Wordwide Limited, London, England, UK)

      Pages: 233-236

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Application of ethanesulfonylethoxycarbonyl (Esc) group for solid phase synthesis in water.2005

    • Author(s)
      Hojo, K., Kita, E., Yamamoto, S., Yamaguchi, F., Maeda, M., Kawasaki, K.
    • Journal Title

      Innovation and Perspectives in Solid Phase Synthesis & Combinatorial Libraries 2004 (Edited by Epton, R.)(Mayflower Wordwide Limited, London, England, UK)

      Pages: 237-240

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Solid-phase peptide synthesis in water. part 3 : a water-soluble N-protecting group, 2-[pheny(methyl)sulfonio]ethoxycarbonyl tetrafluoroborate, and its application to solid phase peptide synthesis in water.2004

    • Author(s)
      Hoji, K., Maeda, M., Kawasaki, K.
    • Journal Title

      Tetrahedron 60

      Pages: 1875-1886

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Peptide synthesis in water IV. preparation of N-ethanesulfonylethoxy-carbonyl(Esc) amino acids and their application to solid phase peptide synthesis2004

    • Author(s)
      Hojo, K., Maeda, M., Smith, T.J., Kita, E., Yamaguchi, F., Yamamoto, F., Kawasaki, K.
    • Journal Title

      Chem.Pharm.Bull. 52

      Pages: 422-427

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] 2-(4-Sulfophenylsulfonyl)ethoxycarbonyl group : a new water-soluble N-protecting group and ots application to solid phase peptide synthesis in water.2004

    • Author(s)
      Hojo, K., Maeda, M., Kawasaki, K.
    • Journal Title

      Tetrahedron Lettters 45

      Pages: 9293-9295

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Design of reagents for preparing water-soluble N-protected amino acids.2004

    • Author(s)
      Hojo, K., Maeda, M., Kawasaki, K.
    • Journal Title

      Innovation and Perspectives in Solid Phase Synthesis & Combinatorial Libraries 2004

      Pages: 233-236

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Solid-phase peptide synthesis in water. part 3 : a water-soluble N-protecting group, 2-[pheny(methyl)sulfonio]ethoxycarbonyl tetrafluoroborate, and its application to solid phase peptide synthesis in water.2004

    • Author(s)
      Hojo, K., Maeda, M., Kawasaki, K.
    • Journal Title

      Tetrahedron 60

      Pages: 1875-1886

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Peptide synthesis in water IV. preparation of N-ethanesulfonylethoxy- carbonyl (Esc) amino acids and their application to solid phase peptide synthesis2004

    • Author(s)
      Hojo, K., Maeda, M., Smith T.J., Kita, E., Yamaguchi, F., Yamamoto, F., Kawasaki, K.
    • Journal Title

      Chem.Pharm.Bull. 52

      Pages: 422-427

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] 2-(4-Sulfophenylsulfonyl)ethoxycarbonyl group : a new water-soluble N-protecting group and ots application to solid phase peptide synthesis in water.2004

    • Author(s)
      Hojo, K., Maeda, M., Kawasaki, K.
    • Journal Title

      Tetrahedron Lett 45

      Pages: 9293-9295

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Solid phase synthesis in water : application of the ethansulfonylethoxycarbonyl (Esc) group.2004

    • Author(s)
      Hojo, K., Kita, E., Yamamoto, S., Yamaguchi, F., Maeda, M., Kawasaki, K.
    • Journal Title

      Peptide Science 2003 (Edited by Ueki, M.)(PROTEIN RESEARCH FOUNDATION, Minoh-shi, Japan)

      Pages: 145-146

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Solid-phase synthesis in water. Part 3 : A water-soluble N-protecting group, 2-[phenyl(methyl)sulfonio]ethoxycarbonyl tetrafluoroborate, and its application to solid phase peptide synthesis in water2004

    • Author(s)
      Keiko Hojo, Mitsuko Maeda, Koichi Kawasaki
    • Journal Title

      Tetrahedron 60

      Pages: 1875-1886

    • Related Report
      2004 Annual Research Report
  • [Journal Article] 2-(4-sulfophenyl)ethoxycarbonyl group : a new water-soluble N-protecting group and its application to solid phase peptide synthesis in water2004

    • Author(s)
      Keiko Hojo, Mitsuko Maeda, Koichi Kawasaki
    • Journal Title

      Tetrahedron Letters 45

      Pages: 9293-9295

    • Related Report
      2004 Annual Research Report
  • [Journal Article] A New Reagent, 2-[Phenyl(methyl)sulfonio]ethyl-4-nitro- phenylcarbonate Tetrafluoroborate (Pms-ONp), for Preparing Water-Soluble N-Protected Amino Acids2003

    • Author(s)
      Hojo, K., Maeda, M., Takahara, Y, Yamamoto, S., Kawasaki, K.
    • Journal Title

      Tetrahedron Lett. 44

      Pages: 2849-2851

    • NAID

      80015974544

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] A Water Soluble N-Protecting Group, 2-[Phenyl(methyl)-sulphonio]ethyloxycarbonyl Tetrafluoroborate and Its Application to Solid Phase Peptide Synthesis in Water.2003

    • Author(s)
      Hojo, K., Maeda, M., Kawasaki, K.
    • Journal Title

      Innovation and Perspectives in Solid Phase Synthesis & Combinatrial Libraries 2002 (Edited by Epton, R.)(Mayflower Wordwide Limited, Kingswinford, England)

      Pages: 211-212

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] A New Reagent, 2-[Phenyl(methyl)sulfonio]ethyl-4-nitro-phenylcarbonate Tetrafluoroborate (Pms-ONp), for Prepareing Water-Soluble N-Protected Amino Acids.2003

    • Author(s)
      Hojo, K., Maeda, M., Kawasaki, K.
    • Journal Title

      Peptide Science 2002 (Edited by Yamada, T.)(PROTEIN RESEARCH FOUNDATION, Minoh-shi, Japan)

      Pages: 153-154

    • NAID

      80015974544

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] A New Reagent, 2-[Phenyl(methyl)sulfonio]ethyl-4-nitro-phenylcarbonate Tetrafluoroborate(Pms-ONp), for Preparing Water-Soluble N-Protected Amino Acids2002

    • Author(s)
      Hojo, K., Maeda, M., Takahara, Y., Yamamoto, S., Kawasaki, K.
    • Journal Title

      Tetrahedron Letters 44

      Pages: 2849-2852

    • NAID

      80015974544

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] A Water Soluble N-Protecting Group, 2-[Phenyl(methyl)-sulphonio]ethyloxycarbonyl Tetrafluoroborate and Its Application to Solid Phase Peptide Synthesis in Water.2002

    • Author(s)
      Hojo, K., Maeda, M., Kawasaki, K.
    • Journal Title

      Peptide Science 2001 (Edited by Aoyagi, H.)(PROTEIN RESEARCH FOUNDATION, Minoh-shi, Japan)

      Pages: 41-42

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Publications] Keiko Hojo, Mitsuko Maeda, Koichi Kawasaki: "Solid phase peptide synthesis in water. III. A water-soluble N-protecting group, 2-[phenyl(methyl)sulfonio]ethoxycarbonyl tetrafluoroborate, and its application to solid phase peptide synthesis"Tetrahedron. 60. 1875-1886 (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] Keiko Hojo, Mitsuko Maeda, Timothy J.Smith, Eriko Kita, Fumie Yamaguchi, Sachiko Yamamoto, Koichi Kawasaki: "Peptide synthesis in water IV. Preparation of N-ethanesulfonylethoxy-Carbonyl (Esc) amino acids and their application to solid phase peptide synthesis"Chem.Pharm.Bull.. 27・4(In press). (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] 北條恵子, 前田光子, 川崎紘一: "A New Reagent, 2-[Phenyl(methyl)sulfonio]ethyl-4-nitrophenylcarbonate Tetrafluoroborate(Pms-ONp), for Preparing Water-soluble N-Protected amino acids"Tetrahedron Letters. 44. 2849-2851 (2003)

    • Related Report
      2002 Annual Research Report

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Published: 2002-04-01   Modified: 2016-04-21  

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