Chemo-enzymatic synthesis of isotopically labelled L-Valine, L-Isoleucine and allo-isoleucine

Autor:	Christine L. Wellis, R. Gordon Reid, Peter L. Winton, Nicholas M. Kelly
Rok vydání:	1996
Předmět:	chemistry.chemical_classification Ketone biology Chemistry Stereochemistry Carboxylic acid Organic Chemistry Leucine dehydrogenase Biochemistry Reductive amination Enzyme Valine Drug Discovery biology.protein Lipase Isoleucine
Zdroj:	Tetrahedron Letters. 37:1517-1520
ISSN:	0040-4039
DOI:	10.1016/0040-4039(96)00053-6
Popis:	Syntheses of (3 R )-[4,4,4-D 3 ]-L-valine, [ 15 N]-L-isoleucine and [ 15 N]- allo -isoleucine from homochiral 2-alkylated carboxylic acids are described. The approach involves a one-carbon homologation of the carboxylic acid to give the corrresponding β-substituted α-keto ester which is converted directly to the α-amino acid in a one-pot procedure involving two enzyme catalysed reactions ( Candida cylindracea lipase to hydroluse the ester and leucine dehydrogenase to catalyse the reductive amination of the ketone). This strategy may be simply adapted for the selective labelling of each site of the L-amino acid.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::9879e40f2606b8e9f58aefd4c3aa89d2 https://doi.org/10.1016/0040-4039(96)00053-6 Zobrazit plný text záznamu Full Text from ScienceDirect