CHEMOSELECTIVE AND ENANTIOSELECTIVE HYDROLYSIS OF NITRILES AND ACID-AMIDES, RESPECTIVELY, WITH RESTING CELLS OF RHODOCOCCUS SP. C3II AND RHODOCOCCUS-ERYTHROPOLIS MP50

The two new bacterial strains, Rhodococcus sp. C3II and Rhodococcus er ythropolis MP50, which have been especially selected for the enantiose lective hydrolysis of pharmaceutically interesting 2-arylpropionitrile s like naproxen nitrile, have been applied for the hydrolysis of vario us aliphatic and aromatic nitriles and acid amides. From the enantiose lective hydrolysis of racemic ibuprofen amide 4, 2-phenylbutyronitrile 5a as well as the profen-related atrolactamide 8 we deduce the decisi ve role of both an alkyl and aryl substituent in the alpha-position to the nitrile or amide function for high enantioselectivity of the hydr olysis. Strain C3II and MP50 differ in the activity of their nitrile h ydratase-amidase enzyme systems. This is of interest for the regiosele ctive hydrolysis of the dinitriles 10a-13a to diacids 10f-13f. While s train C3II is suitable to preferentially produce mononitrile monoamide derivatives, strain MP50 can be used especially to form mononitrile m onoacid and monoamide monoacid derivatives. (C) 1998 Elsevier Science B.V. All rights reserved.