Chemoselective Elaboration of O-Linked Glycopeptide Mimetics by Alkylation of 3-ThioGalNAc
- 1 February 2001
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 123 (8) , 1587-1595
- https://doi.org/10.1021/ja003713q
Abstract
A critical branch point in mucin-type oligosaccharides is the β1 → 3 glycosidic linkage to the core α-N-acetylgalactosamine (GalNAc) residue. We report here a strategy for the synthesis of O-linked glycopeptide analogues that replaces this linkage with a thioether amenable to construction by chemoselective ligation. The key building block was a 2-azido-3-thiogalactose-Thr analogue that was incorporated into a peptide by fluorenylmethoxycarbonyl (Fmoc)-based solid-phase peptide synthesis. Higher order oligosaccharides were readily generated by alkylation of the corresponding 3-thioGalNAc with N-bromoacetamido sugars. The rapid assembly of “core 1”and “core 3” O-linked glycopeptide mimetics was accomplished in this fashion.Keywords
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