Mechanism of hydroxylation of biphenyl by Cunninghamella echinulata.

The hydroxylation of [U-2H]biphenyl and [2,2',3,3',5,5',6,6'-2H]biphenyl by Cunninghamella echinulata A.T.C.C. 9244 has been studied. G.l.c.-mass-spectrometry analyses indicate the lack of an isotope effect during the hydroxylation of the perdeuterated substrate. Both g.l.c.-mass spectrometry and 1H n.m.r. were used to definitively demonstrate the presence of a 1,2-hydride-shift during the microbiological hydroxylation of [2,2',3,3',5,5',6,6'-2H]biphenyl.