Enantioconvergent Hydrolysis of Styrene Epoxides by Newly Discovered Epoxide Hydrolases in Mung Bean

2006 ◽  
Vol 8 (8) ◽  
pp. 1737-1740 ◽  
Author(s):  
Wei Xu ◽  
Jian-He Xu ◽  
Jiang Pan ◽  
Qing Gu ◽  
Xin-Yan Wu
Keyword(s):  
Mung Bean ◽  
Epoxide Hydrolases ◽  
Enantioconvergent Hydrolysis ◽  
Hydrolysis Of

Previously published / Prédémment paruAsymmetric total synthesis of (+)-exo-brevicomin based on enantioconvergent biocatalytic hydrolysis of an alkene-functionalized 2,3-disubstituted epoxide

2002 ◽  
Vol 80 (6) ◽  
Author(s):  
Sandra F Mayer ◽  
Harald Mang ◽  
Andreas Steinreiber ◽  
Robert Saf ◽  
Kurt Faber
Keyword(s):  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Bark Beetle ◽  
Epoxide Hydrolase ◽  
Side Chains ◽  
Beetle Species ◽  
Epoxide Hydrolases ◽  
Pheromone System ◽  
Enantioconvergent Hydrolysis ◽  
Hydrolysis Of

A short total asymmetric synthesis of (+)-exo- and (–)-endo-brevicomin ((+)-exo-3 and (–)-endo-3), which are components of the attracting pheromone system of several bark-beetle species belonging to the genera Dendroctonus and Dryocoetes, was accomplished via a chemoenzymatic protocol. The key step consisted of biocatalytic hydrolysis by bacterial epoxide hydrolases of cis-configured 2,3-disubstituted oxiranes bearing olefinic side chains. This reaction proceeded in an enantioconvergent fashion, by affording a single enantiomeric vic-diol from the rac-epoxide in up to 92% ee and 83% isolated yield.Key words: bacterial epoxide hydrolase, 2,3-disubstituted oxirane, enantioconvergent hydrolysis, (+)-exo-brevicomin, (–)-endo-brevicomin.

Use of hydrophilic ionic liquids in a two-phase system to improve Mung bean epoxide hydrolases-mediated asymmetric hydrolysis of styrene oxide

2012 ◽  
Vol 162 (2-3) ◽  
pp. 183-190 ◽  
Author(s):  
Wen-Jing Chen ◽  
Wen-Yong Lou ◽  
Chun-Yang Yu ◽  
Hong Wu ◽  
Min-Hua Zong ◽  
...  
Keyword(s):  
Ionic Liquids ◽  
Mung Bean ◽  
Styrene Oxide ◽  
Phase System ◽  
Two Phase ◽  
Epoxide Hydrolases ◽  
Hydrolysis Of

Efficient asymmetric hydrolysis of styrene oxide by Mung bean epoxide hydrolases in a supercritical CO2/buffer biphasic system

2018 ◽  
Vol 28 ◽  
pp. 216-220
Author(s):  
Bin Wang ◽  
Qinting He ◽  
Li Shu ◽  
Fengli Yang ◽  
Guobin Liang ◽  
...  
Keyword(s):  
Mung Bean ◽  
Supercritical Co2 ◽  
Styrene Oxide ◽  
Biphasic System ◽  
Epoxide Hydrolases ◽  
Hydrolysis Of

Asymmetric total synthesis of (+)-exo-brevicomin based on enantioconvergent biocatalytic hydrolysis of an alkene-functionalized 2,3-disubstituted epoxide

2002 ◽  
Vol 80 (4) ◽  
pp. 362-369 ◽  
Author(s):  
Sandra F Mayer ◽  
Harald Mang ◽  
Andreas Steinreiber ◽  
Robert Saf ◽  
Kurt Faber
Keyword(s):  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Bark Beetle ◽  
Epoxide Hydrolase ◽  
Beetle Species ◽  
Asymmetric Total Synthesis ◽  
Epoxide Hydrolases ◽  
Pheromone System ◽  
Enantioconvergent Hydrolysis ◽  
Hydrolysis Of

A short total asymmetric synthesis of (+)-exo- and (–)-endo-brevicomin ((+)-exo-3 and (–)-endo-3), which are components of the attracting pheromone system of several bark-beetle species belonging to the genera Dendroctonus and Dryocoetes, was accomplished via a chemoenzymatic protocol. The key step consisted of biocatalytic hydrolysis by bacterial epoxide hydrolases of cis-configured 2,3-disubstituted oxiranes bearing olefinic side chains. This reaction proceeded in an enantioconvergent fashion, by affording a single enantiomeric vic-diol from the rac-epoxide in up to 92% ee and 83% isolated yield.Key words: bacterial epoxide hydrolase, 2,3-disubstituted oxirane, enantioconvergent hydrolysis, (+)-exo-brevicomin, (–)-endo-brevicomin.

scholarly journals Stereoselective hydrolysis of epoxy‐eicosanoids by mammalian soluble epoxide hydrolases

2008 ◽  
Vol 22 (S1) ◽  
Author(s):  
Cosima Schmidt ◽  
Robert Fischer ◽  
Marija Markovic ◽  
Christophe Morisseau ◽  
Bruce D. Hammock ◽  
...  
Keyword(s):  
Epoxide Hydrolases ◽  
Stereoselective Hydrolysis ◽  
Hydrolysis Of
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