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Enantioselective Preparation of δ‐Valerolactones with Horse Liver Alcohol Dehydrogenase
Author(s) -
DíazRodríguez Alba,
IglesiasFernández Javier,
Rovira Carme,
GotorFernández Vicente
Publication year - 2014
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201300640
Subject(s) - desymmetrization , enantioselective synthesis , chemistry , alcohol dehydrogenase , stereoselectivity , biocatalysis , catalysis , tetrahydrofuran , cofactor , enantiomeric excess , alcohol , enantiomer , selectivity , organic chemistry , stereochemistry , combinatorial chemistry , reaction mechanism , enzyme , solvent
Horse liver alcohol dehydrogenase (HLADH) has been found to be a versatile biocatalyst for the desymmetrization of prochiral 3‐arylpentane‐1,5‐diols, based on a two‐step one‐pot oxidation. This procedure has allowed the formation of valuable ( S )‐lactones in good to excellent conversions and enantiomeric excess. The catalytic performance of HLADH has been studied using several cofactor regeneration systems and cosolvents, finding great improvements in terms of activity with L‐lactate dehydrogenase, while the stereoselectivity of the process was significantly improved when using tetrahydrofuran. Docking studies has revealed the pattern substitution importance in the selectivity and activity of this oxidative process.