Branched building units for synthesizing cyclic peptides

US6184345A · kind A · utility

Assignee

• Peptor Ltd. · IL

Inventors

• Siegmund Reissmann · Jena, DE
• Bettina Muller · Jena, DE
• Peter Kleinwachter · Hermsdorf, DE
• Diana Besser · Jena, DE

Key dates

• Filing date: Feb 8, 1999
• Grant date: Feb 6, 2001
• Expiry date: Feb 8, 2019

Classification

• Technology area (CPC Y): Emerging Cross-Sectional Technologies
• CPC primary: Y02P20/55
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention relates to building units suitable for the synthesis of backbone cyclized peptides. The building units of this invention have structures of Formula (I): EQU X--AA.sub.m --U--AA.sub.p --Y (I) wherein AA.sub.m and AA.sub.p are residues of natural or synthetic amino acids and U is C.sup..alpha. ON[(CH.sub.2).sub.n+1 W] or .PSI.(C.sup..alpha. H.sub.2 N)[CO(CH.sub.2).sub.q W], in which C.sup..alpha. is a carbon atom and is the .alpha. carbon of AA.sub.m if m>0. W is NH--X or COY, and X is H, Boc, Z, Fmoc, or Alloc while Y is the hydroxyl group of a carboxylic acid moiety or a carboxylic acid protecting group. The letter m refers to an integer from 0 to 10; n is a number from 0 to 6; p is a number from 1 to 10; and q is a number from 1 to 6. The present invention is also directed to methods of synthesizing building units of Formula (I) via different routes.