Glycopeptide antibiotics, combinational libraries of glycopeptide antibiotics and methods of producing same

Abstract

Methods for preparing a glycopeptide are disclosed. The methods comprise the steps of selecting a protected glycopeptide of the formula A1-A2-A3-A4-A5-A6-A7, wherein the groups A1 to A7 comprise the heptapeptide structure of naturally occurring vancomycin; at least A4 is linked to a glycosidic group which has a hexose residue linked to A4; and the protected glycopeptide has no free amino or carboxyl groups and has a free primary hydroxyl group only at the 6-position of said hexose residue. The protected glycopeptide is contacted with a compound of the formula ArSO2G where Ar is an aryl group and G is a leaving group under conditions effective to allow reaction of said free primary hydroxyl group to form a glycopeptide sulfonate ester; and the glycopeptide sulfonate ester is contacted with a nucleophile under conditions effective to allow displacement of a sulfonate group to produce a substituted glycopeptide.

Dependencies are inferred from the claim text.