Synthesis of an isostere of an O-linked glycopeptide

Lisa J Whalen; Randall L Halcomb

doi:10.1021/ol0490779

Synthesis of an isostere of an O-linked glycopeptide

Org Lett. 2004 Sep 16;6(19):3221-4. doi: 10.1021/ol0490779.

Authors

Lisa J Whalen¹, Randall L Halcomb

Affiliation

¹ Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309-0215, USA.

PMID: 15355017
DOI: 10.1021/ol0490779

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.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Catalysis
Galactose / chemistry
Glycopeptides / chemical synthesis*
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular

Substances

Glycopeptides
Galactose