C-Linked glycosyl azido acid in novel solid-phase C-glycopeptide synthesis

A C-linked glycosyl decapeptide was synthesised on solid-phase by a combination of the Fmoc-method and a novel method of using azido acids with reductive deprotection. The unprotected C-glycosyl azido acid building block was incorparated by a TBTU coupling, subsequently reduced using DTT in DMF and...

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Bibliographic Details
Published in:Tetrahedron letters 1998-03, Vol.39 (13), p.1815-1818
Main Authors: Tedebark, Ulf, Meldal, Morten, Panza, Luigi, Bock, Klaus
Format: Article
Language:English
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Summary:A C-linked glycosyl decapeptide was synthesised on solid-phase by a combination of the Fmoc-method and a novel method of using azido acids with reductive deprotection. The unprotected C-glycosyl azido acid building block was incorparated by a TBTU coupling, subsequently reduced using DTT in DMF and followed by further Fmoc-amino acid-OPfp ester couplings. Mouse hemoglobin (67–76) carrying the C-linked glycoside in position 72 was prepared as a metabolically stable T-cell glycopeptide antigen. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(98)00095-1