Highly enantioselective reduction of beta,beta-disubstituted aromatic nitroalkenes catalyzed by Clostridium sporogenes.
This is the first report of the use of Clostridium sporogenes extracts for enantioselective reduction of CC double bonds of beta,beta-disubstituted (1) and alpha,beta-disubstituted nitroalkenes (3). Crude enzyme preparations reduced aryl derivatives 1a-e and 1h, in 35-86% yield with > or =97% ee. Reduction of (E)- and (Z)-isomers of 1c gave the same enantiomer of 2c (> or =99% ee). In contrast, alpha,beta-disubstituted nitroalkene 3a was a poor substrate, yielding (S)- 4a in low yield (10-20%), and the ee (30-70% ee) depended on NADH concentration. An efficient synthesis of a library of nitroalkenes 1 is described.
Fryszkowska
Anna
A
Manchester Interdisciplinary Biocentre, University of Manchester, 131 Princess Street, Manchester, United Kingdom.
Fisher
Karl
K
Gardiner
John M
JM
Stephens
Gill M
GM
D000475:Alkenes / Q000378:metabolism*; D001711:Biotransformation; D002384:Catalysis; D003013:Clostridium / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism
D000475:Alkenes