Chemoenzymatic Synthesis of Enantiomerically Pure (2 S  , 3 R  , 4 S )‐4‐Hydroxyisoleucine, an Insulinotropic Amino Acid Isolated from Fenugreek Seeds | Zendy

RollandFulcrand Valérie | Zendy; Rolland Marc | Zendy; Roumestant MarieLouise | Zendy; Martinez Jean | Zendy

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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)

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