134937-40-9Relevant academic research and scientific papers
Microbial deracemization of α-substituted carboxylic acids: Control of the reaction path
Kato, Dai-Ichiro,Miyamoto, Kenji,Ohta, Hiromichi
, p. 2965 - 2973 (2007/10/03)
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.
Microbial deracemization of α-substituted carboxylic acids: Substrate specificity and mechanistic investigation
Kato, Dai-Ichiro,Mitsuda, Satoshi,Ohta, Hiromichi
, p. 7234 - 7242 (2007/10/03)
A new enzymatic method for the preparation of optically active α-substituted carboxylic acids is reported. This technique is called deracemization reaction, which provides us with a route to obtain the enantiomerically pure compounds, theoretically in 100% yield starting from the racemic mixture. This means that the synthesis of a racemate is almost equal to the synthesis of the optically active compound, and this concept is entirely different from the commonly accepted one in the asymmetric synthesis. Using the growing cell system of Nocardia diaphanozonaria JCM3208, racemates of 2-aryl- and 2-aryloxypropanoic acid are deracemized smoothly and (R)-form-enriched products are recovered in high chemical yield (>50%). In addition, using optically active starting compounds and deuterated derivatives as well as inhibitors, we have disclosed the fact that a new type of enzyme takes part in this biotransformation, and that the reaction proceeds probably via the same mechanism as that in rat liver.
SYNTHESIS OF 2-ARYLSULFONYLISOVALERIC ACIDS
Polanski, Jaroslaw,Ratajczak, Aleksander
, p. 1973 - 1977 (2007/10/02)
Following the rules of a systematic QSAR study aimed at designing new, more potent sweeteners, the synthesis of 2-arylsulfonylisovaleric acids was carried out.
