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

Abstract

A glycopeptide of the formula A-A-A-A-A-A-A, in which each dash represents a covalent bond; wherein Acomprises a modified or unmodified α-amino acid residue, alkyl, aryl, aralkyl, alkanoyl, aroyl, aralkanoyl, heterocyclic, heterocyclic-carbonyl, heterocyclic-alkyl, heterocyclic-alkyl-carbonyl, alkylsulfonyl, arylsulfonyl, guanidinyl, carbamoyl, or xanthyl; wherein each of Ato Acomprises a modified or unmodified α-amino acid residue, whereby (i) Ais linked to an amino group on A, (ii) each of A, Aand Abears an aromatic side chain, which aromatic side chains are cross-linked together by two or more covalent bonds, and (iii) Abears a terminal carboxyl, ester, amide, or N-substituted amide group; A chemical library comprising a plurality of the glycopeptides of the invention. A method for preparing a glycopeptide by glycosylation of an aglycone derived from a glycopeptide antibiotic. A method for preparing a glycopeptide by preparing a pseudoaglycone from a glycopeptide antibiotic and glycosylating the pseudoaglycone.