NOVEL PROCESS FOR THE SYNTHESIS OF EXOCHELINS

A process for the synthesis of an Exochelin comprising the steps of generati ng 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, provid...

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Bibliographische Detailangaben
Hauptverfasser:	WEGLARZ, MICHAEL A, GAUDIOSO, LARRY A
Format:	Patent
Sprache:	eng ; fre
Schlagworte:	APPARATUS THEREFOR BEER BIOCHEMISTRY CHEMISTRY ENZYMOLOGY FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIREDCHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERSFROM A RACEMIC MIXTURE GENERAL METHODS OF ORGANIC CHEMISTRY METALLURGY MICROBIOLOGY MUTATION OR GENETIC ENGINEERING ORGANIC CHEMISTRY PEPTIDES SPIRITS VINEGAR WINE
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Beschreibung
Zusammenfassung:	A process for the synthesis of an Exochelin comprising the steps of generati ng 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-N2-Boc-N6- methyl,N6-(benzyloxy) lysine 2-trimethylsilylethyl ester which incorporates the dicarboxylic acid as modified above, removing the N-tert-butoxycarbonyl protecting group from the L-N2-Boc-N6-methyl,N6-(benzyloxy) lysine 2- trimethylsilylethyl ester to yield a substituted lysine, and coupling the sa me with the L-N-[2-benzyloxy(benzoyl) serine or -threonine to yield a 2-trimeth yl 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. Moreparticularly, a synthesis for Exochelin 786SM (R) is disclosed wherein the dicarboxylic acid is suberic ac id and the serine form is utilized.