scholarly journals Accessing Enantiopure Epoxides and Sulfoxides: Related Flavin‐Dependent Monooxygenases Provide Reversed Enantioselectivity

ChemCatChem ◽  
2019 ◽  
Vol 12 (1) ◽  
pp. 199-209 ◽  
Author(s):  
Thomas Heine ◽  
Anika Scholtissek ◽  
Sarah Hofmann ◽  
Rainhard Koch ◽  
Dirk Tischler
Keyword(s):  
Enantiopure Epoxides

SYNTHESIS OF ENANTIOPURE EPOXIDES THROUGH BIOCATALYTIC APPROACHES

1997 ◽  
Vol 51 (1) ◽  
pp. 491-525 ◽  
Author(s):  
A. Archelas ◽  
and R. Furstoss
Keyword(s):  
Enantiopure Epoxides

ChemInform Abstract: Enantiopure Epoxides: Access via Chemical or Enzymatic Routes

ChemInform ◽  
2010 ◽  
Vol 27 (7) ◽  
pp. no-no
Author(s):  
S. PEDRAGOSA-MOREAU ◽  
A. ARCHELAS ◽  
R. FURSTOSS
Keyword(s):  
Enantiopure Epoxides

ChemInform Abstract: Biocatalytic Approaches for the Synthesis of Enantiopure Epoxides

ChemInform ◽  
2010 ◽  
Vol 30 (23) ◽  
pp. no-no
Author(s):  
A. Archelas ◽  
R. Furstoss
Keyword(s):  
Enantiopure Epoxides

ChemInform Abstract: Synthesis of Enantiopure 1,2-Azido and 1,2-Amino Alcohols via Regio- and Stereoselective Ring-Opening of Enantiopure Epoxides by Sodium Azide in Hot Water.

ChemInform ◽  
2016 ◽  
Vol 47 (24) ◽  
Author(s):  
Hai-Yang Wang ◽  
Kun Huang ◽  
Melvin De Jesus ◽  
Sandraliz Espinosa ◽  
Luis E. Pinero-Santiago ◽  
...  
Keyword(s):  
Sodium Azide ◽  
Ring Opening ◽  
Amino Alcohols ◽  
Hot Water ◽  
Enantiopure Epoxides

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.

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