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Enantioselective microbial hydrolysis of dissymmetrical cyclic carbonates with disubstitution |
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| Authors: | Masaki Nogawa Rie Iizuka Hiromichi Ohta Kazutsugu Matsumoto |
| Institution: | a Department of Chemistry, Meisei University, Hodokubo 2-1-1, Hino, Tokyo 191-8506, Japan b Department of Biosciences and Informatics, Keio University, Hiyoshi 3-14-1, Yokohama 223-8522, Japan c Department of Applied Chemistry and Biotechnology, University of Fukui, Bunkyo 3-9-1, Fukui 910-8507, Japan |
| Abstract: | Enantioselective microbial hydrolysis of C1 and C2 dissymmetrical cyclic carbonates with disubstitution (methyl and another groups) has been developed. Pseudomonas diminuta (FU0090), a bacterium, efficiently catalyzes the hydrolysis of five-membered cyclic carbonates. While the trans-substrates are hydrolyzed with low enantioselectivities and/or reactivities, the microbe hydrolyzes the cis-substrates with very high enantioselectivities to afford the corresponding almost optically pure anti-(2R,3S)-diols. On the other hand, six-membered trans-cyclic carbonates are enantioselectively hydrolyzed to afford the corresponding optically active syn-(2R,4R)-diols, although the hydrolysis of the cis-substrates gives racemic compounds. In all cases, the enzyme prefers the (R)-enantiomer for the carbon atom bearing a methyl group. |
| Keywords: | Cyclic carbonates Enantioselective hydrolysis Enzymes Microbial reaction Optically active diols |
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