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Facile Synthesis of Enantiopure 4‐Substituted 2‐Hydroxy‐4‐ butyrolactones using a Robust Fusarium Lactonase
Author(s) -
Chen Bing,
Yin HaiFeng,
Wang ZhenSheng,
Xu JianHe,
Fan LiQiang,
Zhao Jian
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900628
Subject(s) - enantiopure drug , chemistry , diastereomer , fusarium proliferatum , stereoselectivity , biocatalysis , substrate (aquarium) , enantiomer , circular dichroism , enantiomeric excess , enzyme catalysis , stereochemistry , enzyme , catalysis , organic chemistry , enantioselective synthesis , mycotoxin , reaction mechanism , oceanography , food science , geology
A facile chemo‐enzymatic process has been developed for producing stereoisomers of 4‐substituted 2‐hydroxy‐4‐butyrolactones with good to excellent enantioselectivity. This process involves an easy separation of the diastereoisomers by column chromatography and efficient enzymatic resolution by whole cells of Escherichia coli JM109 expressing Fusarium proliferatum lactonase gene. This biocatalyst shows strong tolerance towards different substrate structures and at least three out four possible isomers could be obtained in excellent enantiomeric purity. Different substrate concentrations (10 mM–200 mM) were examined, giving a substrate to catalyst ratio of up to 26:1. This general and efficient enzymatic process provides access to stereoisomers of 4‐substituted 2‐hydroxy‐4‐butyrolactones readily and cost‐effectively. The stereochemical assignments were conducted systematically based on NMR, X‐ray diffraction and circular dichroism, leading to further understanding of the enzyme’s stereoselectivity.