The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.
The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.
Patent No.:
Date of Patent:
May. 16, 2000
Filed:
Aug. 14, 1998
Larry A Gaudioso, Salt Lake City, UT (US);
Michael A Weglarz, Salt Lake City, UT (US);
Keystone BioMedical, Inc., Los Angeles, CA (US);
Abstract
A process for the synthesis of an Exochelin comprising the steps of generating L-N-[(2-benzyloxy-(benzoyl)] serine or L-N-[2-benzyloxy (benzoyl)] threonine, creating L-N-t-Boc-.epsilon.-hydroxynorleucine and reacting same to produce L-N-Boc-.epsilon.-bromonorleucine trimethylsilylethyl ester, providing a dicarboxylic acid and forming an O-benzyl methyl hydroxamate from the dicarboxylic acid, coupling the O-benzyl methyl hydroxamate with the L-N-Boc-.epsilon.-bromonorleucine trimethylsilylethyl ester to give an L-N.sup.2 -Boc-N.sup.6 -methyl,N.sup.6 -(benzyloxy) lysine 2-trimethylsilylethyl ester which incorporates the dicarboxylic acid as modified above, removing the N-tert-butoxycarbonyl protecting group from the L-N.sup.2 -Boc-N.sup.6 -methyl, 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 or -threonine 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 the 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. More particularly, a synthesis for Exochelin 786SM (R) is disclosed wherein the dicarboxylic acid is suberic acid and the serine form is utilized.