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

US7473671B2 · kind B2 · utility

Assignee

• THE TRUSTEES OF PRINCETON UNIVERSITY · US

Inventors

• Daniel Kahne · Brookline, US
• Robert Kerns · Iowa City, US
• Seketsu Fukuzawa · Tokyo, JP
• Min Ge · Nanjing, CN
• Christopher Thompson · Gaithersburg, US

Key dates

• Filing date: Jul 31, 2003
• Grant date: Jan 6, 2009
• Expiry date: Jul 31, 2023

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07K9/008
• WIPO field: Biotechnology
• WIPO sector: Chemistry

Abstract

A glycopeptide of the formula A1-A2-A3-A4-A5-A6-A7, in which each dash represents a covalent bond; wherein A1 comprises 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 A2 to A7 comprises a modified or unmodified α-amino acid residue, whereby (i) A1 is linked to an amino group on A2, (ii) each of A2, A4 and A6 bears an aromatic side chain, which aromatic side chains are cross-linked together by two or more covalent bonds, and (iii) A7 bears 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.