Patent ID: 6063919
Filing Date: 2000-05-16
Classification: C07K,Y02P

Abstract:
A process for the synthesis of Exochelin 786SM(R) comprising the steps of:generating N-(2-benzyloxy-benzoyl)-L-serine;creating N-t-Boc-L-.epsilon.-hydroxynorleucine and reacting same to produce L-N-Boc-.epsilon.-bromonorleucine trimethylsilylethyl ester;coupling O-benzyl methyl suberyl hydroxamate with the L-N-Boc-.epsilon.-bromonorleucine trimethylsilylethyl ester to give L-N.sup.2 -Boc-N.sup.6 -methylsuberyl, N.sup.6 -(benzyloxy) lysine 2-trimethylsilylethyl ester;removing the N-tert-butoxycarbonyl protecting group of L-N.sup.2 -Boc-N.sup.6 -methylsuberyl, N.sup.6 -(benzyloxy) lysine 2-trimethylsilylethyl ester to yield a substituted lysine, and coupling the same with the L- N-[2-benzyloxy-(benzoyl)]serine to yield a 2-trimethyl silylethyl ester of dibenzyl Exochelic acid;transforming the 2-trimethyl silylethyl ester of dibenzyl Exochelic acid to dibenzyl Exochelic acid;preparing benzyl epi-cobactin;forming an ester bond between dibenzyl Exochelic acid and benzyl epi-cobactin to form an intermediate; and,hydrogenolytically removing three benzyl groups from said intermediate, resulting in the synthesized Exochelin 786SM(R).