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Chemoenzymatic Synthesis of Enantiomerically Pure (2 S , 3 R , 4 S )‐4‐Hydroxyisoleucine, an Insulinotropic Amino Acid Isolated from Fenugreek Seeds
Author(s) -
RollandFulcrand Valérie,
Rolland Marc,
Roumestant MarieLouise,
Martinez Jean
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300434
Subject(s) - chemistry , stereochemistry , hydrolysis , derivative (finance) , enantioselective synthesis , kinetic resolution , enzyme , enzymatic hydrolysis , lactone , resolution (logic) , organic chemistry , catalysis , artificial intelligence , computer science , financial economics , economics
A short six‐step synthesis of (2 S ,3 R ,4 S )‐4‐hydroxyisoleucine ( 1a ) with total control of stereochemistry is reported, the last step being the enzymatic resolution by hydrolysis of a N ‐phenylacetyl lactone derivative using the commercially available penicillin acylase G immobilized on Eupergit C (E‐PAC). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)