APPROACH TO USE OF BENZYLPENICILLINACYLASE FOR CONFIGURATIONAL CORRELATIONS OF AMINO-COMPOUNDS

Benzylpenicillinacylase (BPA) from Escherichia coli ATCC 9637 was found capable of hydrolyzing, in addition to the N-acyl derivatives of α -amino acids, the N-phenylacetyl derivatives of a variety of primary amino compounds. An approach to the use of the stereospecific action of BPA for correlating the absolute configurations of amino compounds is described. For this purpose enzymatic hydrolysis of several N-phenylacetylamino derivatives with known absolute configuration was examined. Reference to a single stereomodel was made to analyze hydrolyt-ic data. The substituents at the asymmetric carbon atoms of the preferred enantiomers were then classified in terms of position occupied inside groups of priority sequences. The priority relations found constitute an empirical guide for stereochemical predictions. For some of the substrates examined the absolute configuration was determined, in the course of the present work, by chemical methods. © 1978, American Chemical Society. All rights reserved.