Synthesis of an isostere of an O-linked glycopeptide |
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Authors: | Whalen Lisa J Halcomb Randall L |
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Institution: | Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309-0215, USA. |
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Abstract: | reaction: see text] A route for the synthesis of an electrophilic, carbocyclic galactose equivalent from D-galactose is described. The strategy utilizes ring-closing metathesis with Grubbs's second-generation catalyst as the key step. The galactose-derived electrophile reacted in an S(N)2 fashion with N-Boc-cysteine methyl ester to provide an alpha-galactosylserine isostere. The method was extended to the synthesis of a glycopeptide isostere. |
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