Title:
METHOD FOR SOLID-PHASE SYNTHESIS OF GLYCOPEPTIDE USING SILICON-CONTAINING PROTECTING GROUP AND SYNTHESIS DEVICE
Document Type and Number:
WIPO Patent Application WO/2010/103857
Kind Code:
A1
Abstract:
Disclosed are a novel method for the synthesis of a glycopeptide by which glycopeptides of various types can be deprotected and excised from a resin, each under weakly acidic to weakly basic conditions, without causing the problems of the epimerization of an amino acid at the α-position and the β-elimination of a sugar residue; a synthesis device therefor; and a synthesis intermediate to be used in synthesizing a glycopeptide. Specifically disclosed are a method for the solid-phase synthesis of a glycopeptide which comprises a step for obtaining a glycopeptide derivative wherein the N-terminus is protected, the C-terminus is immobilized to a solid phase via a silicon linker, and a reactive group carried by a sugar residue and a reactive group carried by an amino acid side chain constituting a peptide are protected by silicon-containing groups, and a step for obtaining the glycopeptide by deprotecting said glycopeptide derivative and releasing the same from the solid phase by treating the glycopeptide derivative with an agent for removing the silicon-containing groups and the silicon linker; a synthesis intermediate to be used in the step for obtaining the glycopeptide derivative in the aforesaid method; and a device for the solid-phase synthesis of a glycopeptide.
Inventors:
NISHIMURA SHIN-ICHIRO
SHIMAWAKI KEN
SHIMAWAKI KEN
Application Number:
PCT/JP2010/001797
Publication Date:
September 16, 2010
Filing Date:
March 12, 2010
Export Citation:
Assignee:
UNIV HOKKAIDO NAT UNIV CORP (JP)
NISHIMURA SHIN-ICHIRO
SHIMAWAKI KEN
NISHIMURA SHIN-ICHIRO
SHIMAWAKI KEN
International Classes:
C07K1/04; C07F7/18; C07H9/04; C07H15/26
Other References:
KEI KAWASAKI ET AL.: "Keiso Hogotai Amino-san Building Block o Mochiita To Peptide Koso Gosei", DAI 43 KAI THE SOCIETY OF POLYMER SCIENCE, JAPAN HOKKAIDO SHIBU KENKYU HAPPYOKAI (2008 NENDO) KOEN YOSHISHU, 3 February 2009 (2009-02-03), pages 12
HERZNER, H. ET AL.: "Synthesis of Glycopeptides Containing Carbohydrate and Peptide Recognition Motifs", CHEM. REV., vol. 100, 2000, pages 4495 - 4537
OHNISHI, Y. ET AL.: "Stereoselective synthesis of a C-glycoside analogue of N-Fmoc- serine beta-N-acetylglucosaminide by ramberg- backlund rearrangement", BIOORG. MED. CHEM. LETT., vol. 12, 2002, pages 997 - 999
ISHII, A. ET AL.: "A Facile Silyl Linker Strategy for the Solid-Phase Synthesis of Protected Glycopeptide: Synthesis of an N-Terminal Fragment of IL-2 (1-10)", TETRAHEDRON, vol. 56, 2000, pages 6235 - 6243, XP004214983, DOI: doi:10.1016/S0040-4020(00)00588-3
SAVIN, K. A. ET AL.: "A New Polymer Support Silylene Linking Method for Hindered Hydroxyl- Bearing Systems", J. ORG. CHEM., vol. 64, 1999, pages 4183 - 4186
"89th Annual Meeting of Chemical Society of Japan in Spring (2009) Koen Yokoshu II, 13 March 2009 (13.03. 2009)", article KEI KAWASAKI ET AL.: "Keiso Hogoki o Mochiita To Peptide no Koso Gosei Kenkyu", pages: 1328
HERZNER, H. ET AL.: "Synthesis of Glycopeptides Containing Carbohydrate and Peptide Recognition Motifs", CHEM. REV., vol. 100, 2000, pages 4495 - 4537
OHNISHI, Y. ET AL.: "Stereoselective synthesis of a C-glycoside analogue of N-Fmoc- serine beta-N-acetylglucosaminide by ramberg- backlund rearrangement", BIOORG. MED. CHEM. LETT., vol. 12, 2002, pages 997 - 999
ISHII, A. ET AL.: "A Facile Silyl Linker Strategy for the Solid-Phase Synthesis of Protected Glycopeptide: Synthesis of an N-Terminal Fragment of IL-2 (1-10)", TETRAHEDRON, vol. 56, 2000, pages 6235 - 6243, XP004214983, DOI: doi:10.1016/S0040-4020(00)00588-3
SAVIN, K. A. ET AL.: "A New Polymer Support Silylene Linking Method for Hindered Hydroxyl- Bearing Systems", J. ORG. CHEM., vol. 64, 1999, pages 4183 - 4186
"89th Annual Meeting of Chemical Society of Japan in Spring (2009) Koen Yokoshu II, 13 March 2009 (13.03. 2009)", article KEI KAWASAKI ET AL.: "Keiso Hogoki o Mochiita To Peptide no Koso Gosei Kenkyu", pages: 1328
Attorney, Agent or Firm:
SIKs & Co. (JP)
Patent business corporation patent firm Sykes (JP)
Patent business corporation patent firm Sykes (JP)
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