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Development of the synthetic method of glycoproteins with homogenous glycan structure oriented toward functional analysis of glycans

Research Project

Project/Area Number 22880033
Research Category

Grant-in-Aid for Research Activity Start-up

Allocation TypeSingle-year Grants
Research Field Bioproduction chemistry/Bioorganic chemistry
Research InstitutionTokai University

Principal Investigator

KATAYAMA Hidekazu  東海大学, 工学部, 講師 (30580857)

Project Period (FY) 2010 – 2011
Project Status Completed (Fiscal Year 2011)
Budget Amount *help
¥3,042,000 (Direct Cost: ¥2,340,000、Indirect Cost: ¥702,000)
Fiscal Year 2011: ¥1,404,000 (Direct Cost: ¥1,080,000、Indirect Cost: ¥324,000)
Fiscal Year 2010: ¥1,638,000 (Direct Cost: ¥1,260,000、Indirect Cost: ¥378,000)
Keywords有機化学 / ペプチド化学 / 糖タンパク質 / 糖ペプチド / S-結合型糖鎖 / Py1RS / sublancin / チオエステル / Pocam基 / チオエステル法 / Mercaptomethyl基 / セグメント縮合反応 / PylRS
Research Abstract

In this study, we tried to develop a novel thiol protecting group which was useful for protecting Cys side chain. As a result, Pocam group could be designed, synthesized and used for solid-phase peptide synthesis and peptide condensation reactions. On the other hand, we tried to synthesize neo-glycoproteins by the combination of bacterial recombinant protein expression system and in vitro glycosylation reaction. As a result, we could prepare a recombinant protein containing a specific functional group. A glycopeptide carrying S-linked glycan which was recently found as a novel post-translational modification was chemically synthesized.

Report

(3 results)
  • 2011 Annual Research Report   Final Research Report ( PDF )
  • 2010 Annual Research Report
  • Research Products

    (17 results)

All 2012 2011 2010

All Journal Article (12 results) (of which Peer Reviewed: 12 results) Presentation (5 results)

  • [Journal Article] Pyrrolysine analogues as substrates for the bacterial pyrrolysyl-tRNA synthetase in vitro and in vivo2012

    • Author(s)
      Hidekazu Katayama, Kayo Nozawa, Osamu Nureki, Yoshiaki Nakahara, Hironobu Hojo
    • Journal Title

      Biosci. Biotechnol. Biochem

      Volume: 76 Pages: 205-208

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Pyrrolysine Analogs as Substrates for Bacterial Pyrrolysyl-tRNA Synthetase in Vitro and in Vivo2012

    • Author(s)
      Hidekazu Katayama, 他4名
    • Journal Title

      Bioscience, Biotechnology, and Biochemistry

      Volume: 76 Issue: 1 Pages: 205-208

    • DOI

      10.1271/bbb.110653

    • NAID

      10030399195

    • ISSN
      0916-8451, 1347-6947
    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Chemical synthesis of the S-linked glycopeptide, sublancin2011

    • Author(s)
      Hidekazu Katayama, Yuya Asahina, Hironobu Hojo
    • Journal Title

      J. Peptide Sci

      Volume: 17 Pages: 818-821

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Efficient preparation of Fmoc-aminoacyl-N-ethylcysteine unit, a key device for the synthesis of peptide thioesters2011

    • Author(s)
      Hironobu Hojo, Hajime Kobayashi, Risa Ubagai, Yuya Asahina, Yuko Nakahara, Hidekazu Katayama, Yukishige Ito, Yoshiaki Nakahara
    • Journal Title

      Org. Biomol. Chem

      Volume: 9 Pages: 6807-6813

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] N-Methy-phenacyl-oxycarbamidomethyl(Pocam) group : a novel thiol protecting group on the solid-phase peptide synthesis and the peptide condensation reactions2011

    • Author(s)
      Hidekazu Katayama, Yoshiaki Nakahara, Hironobu Hojo
    • Journal Title

      Org. Biomol. Chem

      Volume: 9 Pages: 4653-4661

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of the sphingolipid activator protein, Saposin C, using an azido-protected O-acyl isopeptide as an aggregation-disrupting element2011

    • Author(s)
      Hironobu Hojo, Hidekazu Katayama, Chiharu Tano, Yuko Nakahara, Azusa Yoneshige, Junko Matsuda, Yohei Sohma, Yoshiaki Kiso, Yoshiaki Nakahara
    • Journal Title

      Tetrahedron Lett

      Volume: 52 Pages: 635-639

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] N-Methyl-phenacyloxycarbamidomethyl (Pocam) group: A novel thiol protecting group for solid-phase peptide synthesis and peptide condensation reactions2011

    • Author(s)
      Hidekazu Katayama, Yoshiaki Nakahara, Hironobu Hojo
    • Journal Title

      Organic and Biomolecular Chemistry

      Volume: 9 Issue: 12 Pages: 4653

    • DOI

      10.1039/c1ob05253e

    • URL

      https://pure.teikyo.jp/en/publications/a4e1d7cd-603c-48f1-9f58-cca974368713

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Efficient preparation of Fmoc-aminoacyl-N-ethylcysteine unit, a key device for the synthesis of peptide thioesters2011

    • Author(s)
      Hironobu Hojo, Hidekazu Katayama, 他6名
    • Journal Title

      Organic and Biomolecular Chemistry

      Volume: 9 Issue: 19 Pages: 6807

    • DOI

      10.1039/c1ob05831b

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Chemical synthesis of the S-linked glycopeptide, sublancin2011

    • Author(s)
      Hidekazu Katayama, Yuya Asahina, Hironobu Hojo
    • Journal Title

      Journal of Peptide Science

      Volume: 17 Issue: 12 Pages: 818

    • DOI

      10.1002/psc.1406

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] The mercaptomethyl group facilitates an efficient one-pot ligation at Xaa-Ser/Thr for(glyco) peptide synthesis2010

    • Author(s)
      Hironobu Hojo, Chinatsu Ozawa, Hidekazu Katayama, Akiharu Ueki, Yuko Nakahara, Yoshiaki Nakahara
    • Journal Title

      Angew. Chem. Int. Ed. Engl

      Volume: 49 Pages: 5318-5321

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] The mercaptomethyl group facilitates an efficient one-pot ligation at Xaa-Ser/Thr for (glyco)peptide synthesis2010

    • Author(s)
      Hironobu Hojo, Hidekazu Katayama, 他4名
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 49 Pages: 5318-5321

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of the sphingolipid activator protein, Saposin C, using an azido-protected O-acyl isopeptide as an aggregation-disrupting element2010

    • Author(s)
      Hironobu Hojo, Hidekazu Katayama, 他7名
    • Journal Title

      Tetrahedron Letters

      Volume: 52 Pages: 635-639

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Presentation] Bacillus subtilis由来S-結合型糖ペプチドsublancinの化学合成2012

    • Author(s)
      片山秀和、朝比奈雄也、北條裕信
    • Organizer
      日本農芸化学会2012年度大会
    • Place of Presentation
      京都女子大学
    • Year and Date
      2012-03-23
    • Related Report
      2011 Annual Research Report 2011 Final Research Report
  • [Presentation] S-結合型糖ペプチドsublancinの化学合成2011

    • Author(s)
      片山秀和、朝比奈雄也、北條裕信
    • Organizer
      第48回ペプチド討論会
    • Place of Presentation
      札幌コンベンションセンター
    • Year and Date
      2011-09-27
    • Related Report
      2011 Annual Research Report 2011 Final Research Report
  • [Presentation] 糖ペプチドセグメント縮合反応におけるラセミ化度の検討2011

    • Author(s)
      片山秀和、北條裕信
    • Organizer
      日本農芸化学会2011年度大会
    • Place of Presentation
      京都女子大学
    • Year and Date
      2011-03-27
    • Related Report
      2011 Final Research Report 2010 Annual Research Report
  • [Presentation] Development of a novel thiol protecting group on the solid phase peptide synthesis and the peptide condensation reaction2010

    • Author(s)
      Hidekazu Katayama, Yoshiaki Nakahara, Hironobu Hojo
    • Organizer
      5^<th> International Peptide Symposium
    • Place of Presentation
      京都国際会館
    • Year and Date
      2010-12-09
    • Related Report
      2011 Final Research Report
  • [Presentation] Development of a novel thiol protecting group on the solid phase peptide synthesis and the peptide condensation reaction2010

    • Author(s)
      Hidekazu Katayama, Yoshiaki Nakahara, Hironobu Hojo
    • Organizer
      5^<th> International Peptide Symposium
    • Place of Presentation
      京都国際会館(京都府)
    • Year and Date
      2010-12-09
    • Related Report
      2010 Annual Research Report

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Published: 2010-08-27   Modified: 2016-04-21  

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