Engineering Commons^™

Biotransformation Of Various Substituted Aromatic Compounds To Chiral Dihydrodihydroxy Derivatives, Henning Raschke, Michael Meier, Roland Hany, Markus D. Muller, Jan Roelof Van Der Meer, Hans-Peter E. Kohler, Joel Gerard Burken

Civil, Architectural and Environmental Engineering Faculty Research & Creative Works

The biotransformation of four different classes of aromatic compounds by the Escherichia coli strain DH5α(pTCB 144), which contained the chlorobenzene dioxygenase (CDO) from Pseudomonas sp. strain P51, was examined. CDO oxidized biphenyl as well as monochlorobiphenyls to the corresponding cis-2,3-dihydro-2,3-dihydroxy derivatives, whereby oxidation occurred on the unsubstituted ring. No higher substituted biphenyls were oxidized. The absolute configurations of several monosubstituted cis-benzene dihydrodiols formed by CDO were determined. All had an S configuration at the carbon atom in meta position to the substituent on the benzene nucleus. with one exception, the enantiomeric excess of several 1,4-disubstituted cis-benzene dihydrodiols formed by CDO …