Preparative-scale kinetic resolution of racemic styrene oxide by immobilized epoxide hydrolase

2011 ◽  
Vol 49 (6-7) ◽  
pp. 555-559 ◽  
Author(s):  
Deniz Yildirim ◽  
S. Seyhan Tükel ◽  
Dilek Alagöz ◽  
Özlem Alptekin
Keyword(s):  
Epoxide Hydrolase ◽  
Kinetic Resolution ◽  
Styrene Oxide ◽  
Preparative Scale

Preparative-Scale Kinetic Resolution of Racemic Styrene Oxide by Immobilized Epoxide Hydrolase

2010 ◽  
Vol 150 ◽  
pp. 378-379
Author(s):  
Deniz Yildirim ◽  
Dilek Alagöz ◽  
Özlem Alptekin ◽  
S.Seyhan Tükel
Keyword(s):  
Epoxide Hydrolase ◽  
Kinetic Resolution ◽  
Styrene Oxide ◽  
Preparative Scale

scholarly journals Enantioselective Hydrolysis of Styrene Oxide and Benzyl Glycidyl Ether by a Variant of Epoxide Hydrolase from Agromyces mediolanus

Marine Drugs ◽  
2019 ◽  
Vol 17 (6) ◽  
pp. 367
Author(s):  
Jin ◽  
Li ◽  
Zhang ◽  
Lin ◽  
Yang ◽  
...  
Keyword(s):  
Epoxide Hydrolase ◽  
Kinetic Resolution ◽  
Styrene Oxide ◽  
Glycidyl Ether ◽  
Enantiomeric Excess ◽  
Docking Simulation ◽  
Optically Active ◽  
Tween 20 ◽  
Enantioselective Hydrolysis ◽  
Enantiopure Epoxides

Enantiopure epoxides are versatile synthetic intermediates for producing optically active pharmaceuticals. In an effort to provide more options for the preparation of enantiopure epoxides, a variant of the epoxide hydrolase (vEH-Am) gene from a marine microorganism Agromyces mediolanus was synthesized and expressed in Escherichia coli. Recombiant vEH-Am displayed a molecular weight of 43 kDa and showed high stability with a half-life of 51.1 h at 30 °C. The purified vEH-Am exhibited high enantioselectivity towards styrene oxide (SO) and benzyl glycidyl ether (BGE). The vEH-Am preferentially converted (S)-SO, leaving (R)-SO with the enantiomeric excess (ee) >99%. However, (R)-BGE was preferentially hydrolyzed by vEH-Am, resulting in (S)-BGE with >99% ee. To investigate the origin of regioselectivity, the interactions between vEH-Am and enantiomers of SO and BGE were analyzed by molecular docking simulation. In addition, it was observed that the yields of (R)-SO and (S)-BGE decreased with the increase of substrate concentrations. The yield of (R)-SO was significantly increased by adding 2% (v/v) Tween-20 or intermittent supplementation of the substrate. To our knowledge, vEH-Am displayed the highest enantioselectivity for the kinetic resolution of racemic BGE among the known EHs, suggesting promising applications of vEH-Am in the preparation of optically active BGE.

mesT, a unique epoxide hydrolase, is essential for optimal growth ofMycobacterium tuberculosisin the presence of styrene oxide

2017 ◽  
Vol 12 (6) ◽  
pp. 527-546 ◽  
Author(s):  
Manisha Chownk ◽  
Aashish Sharma ◽  
Kashmir Singh ◽  
Jagdeep Kaur
Keyword(s):  
Epoxide Hydrolase ◽  
Styrene Oxide ◽  
Optimal Growth
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