Chemoselective ligation applied to the synthesis of a biantennary N-linked glycoform of CD52 |
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Authors: | Pratt Matthew R Bertozzi Carolyn R |
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Institution: | Department of Chemistry, University of California, Berkeley 94720, USA. |
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Abstract: | We report here a strategy for the synthesis of N-linked glycopeptide analogues that replace the glycosidic linkages extending from the core pentasaccharide with thioethers amenable to construction by chemoselective ligation. The key building block, a pentasaccharide-Asn analogue containing two thiol residues, was incorporated into CD52 by 9-fluorenylmethoxycarbonyl (Fmoc)-based solid-phase peptide synthesis. An undecasaccharide mimetic was then readily generated by alkylation of this glycopeptide with an N-bromoacetamido trisaccharide. The rapid assembly of a complex type N-linked glycopeptide mimetic was accomplished using this technique. |
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