TY - JOUR
T1 - Microbial deracemization of α-substituted carboxylic acids
T2 - Control of the reaction path
AU - Kato, Dai Ichiro
AU - Miyamoto, Kenji
AU - Ohta, Hiromichi
N1 - Funding Information:
D.K. acknowledges the financial support by Research Fellowships of the Japan Society for the Promotion of Science for Young Scientists (JSPS Research Fellowships for Young Scientists). This study was performed through Special Coordination Funds for Promoting Science and Technology from the Ministry of Education, Culture, Sports, Science, and Technology, the Japanese Government.
PY - 2004/9/20
Y1 - 2004/9/20
N2 - A novel approach to preparing optically active α-substituted carboxylic acids using the whole cells of Nocardia diaphanozonaria JCM 3208 is described. When 2-phenylthiopropanoic acid and 2-methyl-3-phenylpropanoic acid were subjected to the reaction under aerobic conditions, the oxidation reaction proceeded preferentially rather than deracemization of these substrates. Herein, we report the design of reaction conditions to increase the deracemization activity in preference to oxidation reactions. In addition, we have successfully detected a metabolic intermediate in the reaction mixture of 2-methyl-3-phenylpropanoic acid, which indicates that the deracemization is a competitive reaction against the α-oxidation pathway of fatty acid metabolism.
AB - A novel approach to preparing optically active α-substituted carboxylic acids using the whole cells of Nocardia diaphanozonaria JCM 3208 is described. When 2-phenylthiopropanoic acid and 2-methyl-3-phenylpropanoic acid were subjected to the reaction under aerobic conditions, the oxidation reaction proceeded preferentially rather than deracemization of these substrates. Herein, we report the design of reaction conditions to increase the deracemization activity in preference to oxidation reactions. In addition, we have successfully detected a metabolic intermediate in the reaction mixture of 2-methyl-3-phenylpropanoic acid, which indicates that the deracemization is a competitive reaction against the α-oxidation pathway of fatty acid metabolism.
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U2 - 10.1016/j.tetasy.2004.06.049
DO - 10.1016/j.tetasy.2004.06.049
M3 - Article
AN - SCOPUS:4644299277
SN - 0957-4166
VL - 15
SP - 2965
EP - 2973
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 18
ER -