Patent ID: 6310180
Filing Date: 2001-10-30
Classification: A61K,C07K,C12N,G01N,Y02P

Abstract:
A method of forming an amide bond between a first molecule and a second molecule, said first and second molecule independently selected from the group consisting of an amino acid, peptide, peptide mimetic, peptide scaffolding matrix and protein, said method comprising coupling said first molecule to said second molecule by means of an acyl rearrangement reaction through a five to seven membered ring intermediate without aid of a template, said coupling selected from the group consisting of(A) a thioesterification reaction comprising reacting a thiocarboxylic acid on either said first molecule or said second molecule with a 1,2-aminohaloethane moiety on either said second molecule or said first molecule, respectively;(B) a thioesterification reaction comprising reacting a thiocarboxylic acid on either said first molecule or said second molecule with a aziridine moiety on either said second molecule or said first molecule, respectively;(C) a disulfide exchange reaction comprising reacting an acyl mixed disulfide on either said first molecule or said second molecule with a 1,2-aminothiol moiety on either said second molecule or said first molecule, respectively;(D) a disulfide exchange reaction comprising reacting a thiocarboxylic moiety on either said first molecule or said second molecule with a 1,2-aminoethane moiety on either said second molecule or said first molecule, respectively;(E) an N-acylation reaction comprising reacting a 1,2-aminoethane imidazole moiety on either said first molecule or said second molecule with an acyl mixed disulfide moiety on either said second molecule or said first molecule, respectively; and(F) an O-acylation reaction comprising reacting a 1,2-aminoethane carboxylic moiety on either said first molecule or said second molecule with an acyl mixed disulfide moiety on either said second molecule or said first molecule, respectively.