title: Synthesis of an isostere of an O-linked glycopeptide.
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.
authors.affiliation: Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309-0215, USA.
authors.forename: Lisa J
authors.initials: LJ
authors.lastname: Whalen
authors.forename: Randall L
authors.initials: RL
authors.lastname: Halcomb
mesh_terms: D002384:Catalysis; D005690:Galactose / Q000737:chemistry; D006020:Glycopeptides / Q000138:chemical synthesis*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular
chemical_list: D006020:Glycopeptides; D005690:Galactose