STRUCTURE AND STEREOCHEMISTRY OF CIS-DIHYDRO DIOL AND PHENOL METABOLITES OF BICYCLIC AZAARENES FROM PSEUDOMONAS-PUTIDA UV4

Biotransformation of quinoline, isoquinoline, quinoxaline and quinazol ine using growing cultures of Pseudomonas putida UV4 yielded cis-dihyd ro diols from the oxidation of the carbocyclic aromatic ring. Aromatic hydroxylation was observed in both carbocyclic and heterocyclic rings . Ring cleavage of the quinoline skeleton to yield anthranilic acid, a nd cis-diol formation (with alkene bond reduction) to yield cis-5,6,7, 8-tetrahydroquinazoline-5,6-diol from quinazoline were observed. The c is-dihydro diol metabolites of quinoline (5,6- and 7,8-) and quinoxali ne (5,6-) were found to be optically pure, while metabolism of isoquin oline gave one homochiral (5,6-) and one racemic (7,8-) cis-dihydro di ol product. The absolute configurations of the cis-dihydro diol metabo lites have been determined using H-1 NMR analyses, stereochemical corr elations and X-ray crystallography methods.