Enantioselective conversion of α-arylnitriles by Klebsiella oxytoca

A new bacterial isolate Klebsiella oxytoca 38.1.2 with stereoselective nitrile hydratase activity against rac-2-phenylglycine nitrile, rac-2-phenylpropionitrile and rac-mandelonitrile was investigated. The cultivation conditions for growth and nitrile hydratase formation were studied. An intracellular (S)-enantioselective nitrile hydratase and a putative (S)-selective amidase were found to be induced in the presence of rac-2-phenylpropionitrile. The temperature dependence on the enantioselectivity of the nitrile hydratase active cells was studied in more detail for the biotransformation of rac-2-phenylpropionitrile and rac-mandelonitrile. By increasing the temperature from 15 degrees C to 37 degrees C, the apparent enantiomeric ratio of the conversion of rac-2-phenylpropionitrile to (S)-2-phenylpropionamide increased from 16 to 35 at nearly 50% conversion rate. rac-Mandelonitrile was converted to (S)-mandelamide with an enantiomeric excess of up to 95% in a 80% yield without further conversion to mandelic acid. (C) 2008 Published by Elsevier Ltd.