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

• Project/Area Number: 22880033
• Research Category: Grant-in-Aid for Research Activity Start-up
• Allocation Type: Single-year Grants
• Research Field: Bioproduction chemistry/Bioorganic chemistry
• Research Institution: Tokai 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: ¥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.

Research Products

• [Journal Article] Pyrrolysine analogues as substrates for the bacterial pyrrolysyl-tRNA synthetase in vitro and in vivo (2012)
  • Author(s): Hidekazu Katayama, Kayo Nozawa, Osamu Nureki, Yoshiaki Nakahara, Hironobu Hojo
  • Journal Title: Biosci. Biotechnol. Biochem Volume: 76 Pages: 205-208
  • Peer Reviewed
• [Journal Article] Pyrrolysine Analogs as Substrates for Bacterial Pyrrolysyl-tRNA Synthetase in Vitro and in Vivo (2012)
  • 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
  • Peer Reviewed
• [Journal Article] Chemical synthesis of the S-linked glycopeptide, sublancin (2011)
  • Author(s): Hidekazu Katayama, Yuya Asahina, Hironobu Hojo
  • Journal Title: J. Peptide Sci Volume: 17 Pages: 818-821
  • Peer Reviewed
• [Journal Article] Efficient preparation of Fmoc-aminoacyl-N-ethylcysteine unit, a key device for the synthesis of peptide thioesters (2011)
  • 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
  • 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 reactions (2011)
  • Author(s): Hidekazu Katayama, Yoshiaki Nakahara, Hironobu Hojo
  • Journal Title: Org. Biomol. Chem Volume: 9 Pages: 4653-4661
  • Peer Reviewed
• [Journal Article] Synthesis of the sphingolipid activator protein, Saposin C, using an azido-protected O-acyl isopeptide as an aggregation-disrupting element (2011)
  • 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
  • Peer Reviewed
• [Journal Article] N-Methyl-phenacyloxycarbamidomethyl (Pocam) group : a novel thiol protecting group on the solid-phase peptide synthesis and the peptide condensation reactions (2011)
  • Author(s): Hidekazu Katayama, Yoshiaki Nakahara, Hironobu Hojo
  • Journal Title: Organic and Biomolecular Chemistry Volume: 9 Issue: 12 Pages: 4653-4661
  • DOI: 10.1039/c1ob05253e
  • Peer Reviewed
• [Journal Article] Efficient preparation of Fmoc-aminoacyl-N-ethylcysteine unit, a key device for the synthesis of peptide thioesters (2011)
  • Author(s): Hironobu Hojo, Hidekazu Katayama, 他6名
  • Journal Title: Organic and Biomolecular Chemistry Volume: 9 Issue: 19 Pages: 6807-6813
  • DOI: 10.1039/c1ob05831b
  • Peer Reviewed
• [Journal Article] Chemical synthesis of the S-linked glycopeptide, sublancin (2011)
  • Author(s): Hidekazu Katayama, Yuya Asahina, Hironobu Hojo
  • Journal Title: Journal of Peptide Science Volume: 17 Issue: 12 Pages: 818-821
  • DOI: 10.1002/psc.1406
  • Peer Reviewed
• [Journal Article] The mercaptomethyl group facilitates an efficient one-pot ligation at Xaa-Ser/Thr for(glyco) peptide synthesis (2010)
  • 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
  • Peer Reviewed
• [Journal Article] The mercaptomethyl group facilitates an efficient one-pot ligation at Xaa-Ser/Thr for (glyco)peptide synthesis (2010)
  • Author(s): Hironobu Hojo, Hidekazu Katayama, 他4名
  • Journal Title: Angewandte Chemie International Edition Volume: 49 Pages: 5318-5321
  • Peer Reviewed
• [Journal Article] Synthesis of the sphingolipid activator protein, Saposin C, using an azido-protected O-acyl isopeptide as an aggregation-disrupting element (2010)
  • Author(s): Hironobu Hojo, Hidekazu Katayama, 他7名
  • Journal Title: Tetrahedron Letters Volume: 52 Pages: 635-639
  • 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
• [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
• [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
• [Presentation] Development of a novel thiol protecting group on the solid phase peptide synthesis and the peptide condensation reaction (2010)
  • 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
• [Presentation] Development of a novel thiol protecting group on the solid phase peptide synthesis and the peptide condensation reaction (2010)
  • 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