Synthesis of asparagine-linked glycopeptides on a polymeric solid support

US5679769A · kind A · utility

Assignee

• Sloan Kettering Institute for Cancer Research · US

Inventors

• Samuel J. Danishefsky · New Haven, US
• Jacques Y. Roberge · Princeton, US
• Xenia Beebe · New York, US

Key dates

• Filing date: Jun 7, 1995
• Grant date: Oct 21, 1997
• Expiry date: Jun 7, 2015

Classification

• Technology area (CPC A): Human Necessities
• CPC primary: A61K2039/876
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

The present invention provides a process for synthesizing a glycopeptide having the structure: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are each independently H, OH, OR.sup.1, NH.sub.2, NHCOR.sup.i, F, CH.sub.2 OH, CH.sub.2 OR.sup.i, or a substituted or unsubstituted linear or branched chain alkyl, arylalkyl or aryl group, where R.sup.i is H, CHO, CO.sub.2 R.sup.ii, a linear or branched chain alkyl, arylalkyl or aryl group, or an oligosaccharide moiety, etc., wherein R.sub.0 is H, a linear or branched chain alkyl, arylalkyl or aryl group; wherein R.sub.10 is a substituted or unsubstituted linear or branched chain acyl, arylacyl or aroyl group; wherein R.sub.11x! represents X amino acid side-chains, and denotes position from the N-terminus, and R.sub.13y! represents Y amino acid side-chains, and denotes position from the C-terminus, wherein a, b, c, h, i, j, r, s and t are each independently an integer between about 0 and about 3; wherein m and n are each independently an integer between about 0 and about 5; and wherein x, x'(N), y and y'(N) are each independently an integer between about 0 and,about 25; such glycopeptides being usef…