The biohydroxylation of a number of cyclic substrates (3-24) containing aro
matic side chains was used to compare substrate specificity and selectivity
of hydroxylation using microbial enzymes and whole-cell biocatalysts. In g
eneral, the regioselectivity of reaction was remarkably similar between the
different catalysts in that little aromatic or benzylic, but significant a
liphatic hydroxylation was observed. However, a more detailed investigation
of isolated products showed complementary substrate specificity, functiona
l group compatibility, and regioselectivity of hydroxylation. Substrate spe
cificity and regioselectivity could be further modulated by small changes t
o the nature of the aromatic side chain, which appears to play an important
role in substrate recognition, (C) 1999 Academic Press.