Chemoselective elaboration of O-linked glycopeptide mimetics by alkylation of 3-thioGalNAc. |
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| Authors: | L A Marcaurelle C R Bertozzi |
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| Institution: | Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, California 94720, USA. |
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| Abstract: | A critical branch point in mucin-type oligosaccharides is the beta 1-->3 glycosidic linkage to the core alpha-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. |
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