• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Elucidation of oligosaccharide function by use of chemical synthesis of glycoprotein

Research Project

Project/Area Number 16550146
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemistry related to living body
Research InstitutionYokohama City University

Principal Investigator

KAJIHARA Yasuhiro  Yokohama City University, International graduate School of Arts and Sciences, Associate Professor, 大学院・国際総合科学研究科, 準教授 (50275020)

Co-Investigator(Kenkyū-buntansha) TSUJI Takashi  University of Tokyo, Department of Industrial Science and Technology Science, 基礎工学部, 助教授 (50339131)
Project Period (FY) 2004 – 2005
Project Status Completed (Fiscal Year 2005)
Budget Amount *help
¥3,700,000 (Direct Cost: ¥3,700,000)
Fiscal Year 2005: ¥1,400,000 (Direct Cost: ¥1,400,000)
Fiscal Year 2004: ¥2,300,000 (Direct Cost: ¥2,300,000)
Keywordsglycopeptide / solid phase peptide synthesis / sialic acid / CTLA4 / 糖鎖 / 糖鎖ペプチド / 糖タンパク
Research Abstract

We developed convenient synthetic method of asparagine-linked sialylglycopeptides. The typical feature of our strategy for the synthesis of a sialylglycopeptide is to employ undecadisialyloligosaccharyl Fmoc-asparagine (Fmoc-Asn(CHO)-OH) without protecting groups on its hydroxyl groups except for the benzyl ester of NeuAc residues. Our synthetic methodology solved the problem of esterification toward sugar hydroxyl groups by activated amino acid during the elongation of a peptide chain. When employing high concentrations of Fmoc-amino acid, esterification markedly occurred, but the esterification scarcely occurred when employing low concentrations of reactants. Taking advantage of these findings, we examined the synthesis of a high molecular sialylglycopeptide, CTLA-4 fragment (113-150) having two complex-type sialyloligosaccharides, by use of native chemical ligation (NCL). As a result, we succeeded in the synthesis of a sialylglycopeptide having a cysteine residue at the N-terminus (CTLA-4:129-150 fragment) and a sialylglycopeptide-thioester (CTLA-4:113-128 fragment). Finally, these synthesized sialylglycopeptides were applied to NCL reaction and the reaction successfully afforded a desired product, CTLA-4 (113-150), having mature and pure complex-type sialyloligosaccharides in excellent purity.

Report

(3 results)
  • 2005 Annual Research Report   Final Research Report Summary
  • 2004 Annual Research Report
  • Research Products

    (14 results)

All 2006 2005 2004 Other

All Journal Article (14 results)

  • [Journal Article] Efficient Synthesis of Sialyiglycopeptides Overcoming Unexpected Aspartimide Formation During Activation of Fmoc-Asn (undecadisialyloligosaccharide) -OH.2006

    • Author(s)
      Naoki Yamamoto, Ayumi Takayanagi, Tohru Sakakibara, Philip E. Dawson, Yasuhiro Kajihara
    • Journal Title

      Tetrahedron Lett. 47

      Pages: 1341-1346

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] An Approach for a Synthesis of Asparagine Linked Sialyiglycopeptides Having Homogeneous Complex Type Undeca-disialyloligosaccharides.2006

    • Author(s)
      Naoki Yamamoto, Ayumi Takayanagi, Ayako Yoshino, Thoru Sakakibara, Yasuhiro Kajihara
    • Journal Title

      Chemistry A European J. (印刷中)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Convenient synthesis of sialylglycopeptide-thioester having an intact and homogeneous complex-type disialyloligosaccharide2006

    • Author(s)
      Yasuhiro, Kajihara, Akiko, Yoshihara, Kiriko, Hirano, Naoki Yamamoto
    • Journal Title

      Carbohydr. Res. (印刷中)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Efficient Synthesis of Sialylglycopeptides Overcoming Unexpected Aspartimide Formation During Activation of Fmoc-Asn(undecadisialyloligosaccharide)-OH.2006

    • Author(s)
      Naoki Yamamoto, Ayumi Takayanagi, Tohru Sakakibara, Philip E. Dawson, Yasuhiro Kajihara
    • Journal Title

      Tetrahedron Lett. 47

      Pages: 1341-1346

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Efficient Synthesis of Sialylglycopeptides Overcoming Unexpected Aspartimide Formation During Activation of Fmoc-Asn (undecadisialyloligosaccharide)-OH.2006

    • Author(s)
      Naoki Yamamoto, Ayumi Takayanagi, Tohru Sakakibara, Philip E.Dawson, Yasuhiro Kajihara
    • Journal Title

      Tetrahedron Lett. 47

      Pages: 1341-1346

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Chemoenzymatic synthesis of diverse asparagine-linked α-(2,3)-sialyloligosaccharides.2006

    • Author(s)
      Yasuhiro Kajihara, Naoki Yamamoto, Tatsuo Miyazaki, Hajime Sato
    • Journal Title

      Curr.Med.Chem. 12

      Pages: 527-550

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Synthesis of diverse asparagine-linked oligosaccharides and synthesis of sialylglycopeptide on solid phase.2005

    • Author(s)
      Yasuhiro Kajihara, Naoki Yamamoto, Tatsuo Miyazaki, Hajime Sato
    • Journal Title

      Curr. Med. Chem. 12

      Pages: 527-550

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Synthesis of diverse asparagine linked oligosaccharides2005

    • Author(s)
      Yasuhiro Kajihara
    • Journal Title

      Journal of Applied Glycoscience 52

      Pages: 177-182

    • NAID

      10014336381

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Synthesis of diverse asparagine-linked oligosaccharides and synthesis of sialylglycopeptide on solid phase.2005

    • Author(s)
      Yasuhiro Kajihara, Naoki Yamamoto, Tatsuo Myazaki, Hajime Sato
    • Journal Title

      Curr.Med.Chem. 12

      Pages: 527-550

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] An Approach for a Synthesis of Asparagine Linked Sialylglycopeptides Having Homogeneous Complex Type Undeca- disialyloligosaccharides.2005

    • Author(s)
      Naoki Yamamoto, Ayumi Takayanagi, Ayako Yoshino, Thoru Sakakibara, Yasuhiro Kajihara
    • Journal Title

      Chemistry A European J. (accepted)

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Synthesis of diverse asparagine linked oligosaccharides and synthesis of sialylglycopentide on solid phase2005

    • Author(s)
      梶原康宏
    • Journal Title

      Current Medicinal Chemistry 12

      Pages: 527-527

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Convenient synthesis of a glycopeptide analogue having a complex type disialyl-undecasaccharide2004

    • Author(s)
      山本直毅
    • Journal Title

      Tetrahedron Letters 45(16)

      Pages: 3287-3287

    • Related Report
      2004 Annual Research Report
  • [Journal Article] An Approach for a Synthesis of Asparagine Linked Sialylglycopeptides Having Homogeneous Complex Type Undeca-disialyloligosaccharides.

    • Author(s)
      Naoki Yamamoto, Ayumi Takayanagi, Ayako Yoshino, Thoru Sakakibara, Yasuhiro Kajihara
    • Journal Title

      Chem.Eur.J. (in press)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Convenient synthesis of sialylglycopeptide-thioester having an intact and homogeneous complex-type disialyloligosaccharide

    • Author(s)
      Yasuhiro, Kajihara, Akiko, Yoshihara, Kiriko, Hirano, Naoki Yamamoto
    • Journal Title

      Carbohydr.Res. (in press)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary

URL: 

Published: 2004-04-01   Modified: 2016-04-21  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi