A Comparative Study of the Synthesis of 3-Substituted Catechols using an Enzymatic and a Chemoenzymatic Method

V. BERBERIAN; C.C. R. ALLEN; N. D. SHARMA; D. R. BOYD; C.HARDACRE

ADVANCED SYNTHESIS & CATALYSIS (PRINT)

WILEY-V C H VERLAG GMBH

Año: 2007 vol. 349 p. 727 - 739

1615-4150

A series of cis dihydrodiol metabolites, available from the bacterial dioxygenase-catalysed oxidation of monosubstituted benzene substrates using Pseudomonas putida UV4 , have been converted to the corresponding catechols using both a heterogeneous catalyst (Pd/C) and a naphthalene cis diol dehydrogenase enzyme present in whole cells of the recombinant strain Escherichia coli DH5(pUC129: nar B). A comparative study of the merits of both routes to 3-substituted catechols has been carried out and the two methods have been found to be complementary. A similarity in mechanism for catechol formation under both enzymatic and chemoenzymatic conditions, involving regioselective oxidation of the hydroxyl group at C-1, has been found using deuterium labelled toluene cis dihydrodiols. The potential, of combining a biocatalytic step (dioxygenase-catalysed cis dihydroxylation) with a chemocatalytic step (Pd/C-catalysed dehydrogenation), into a one-pot route to catechols, from the parent substituted benzene substrates, has been realised.