PMID: 9190820Jun 1, 1997Paper

Stereochemical course of two arene-cis-diol dehydrogenases specifically induced in Pseudomonas putida

Journal of Bacteriology
B MorawskiD W Ribbons

Abstract

Catabolism of nonphenolic arenes is frequently initiated by dioxygenases, yielding single isomer products with two adjacent hydroxylated asymmetric centers. The next enzymic reaction dehydrogenates these cyclic cis-diols, with aromatization yielding catechols for ring cleavage. There are two stereochemical questions to answer. (i) To which face of NAD is hydride transferred giving NADH? (ii) Which hydrogen of the arene-cis-diols is donated to NAD? We report the results of 1H nuclear magnetic resonance [1H NMR] experiments for two diol dehydrogenases induced during growth of Pseudomonas putida PaW1(TOL) and JT105 with p-xylene and p-toluate, respectively. per-[2H5]benzoate-1,2-dihydrodiol and per-[2H7]- and specifically [2H]p-toluate-2,3-dihydrodiols were the substrates used to examine this by 1H NMR, as the two protons of the prochiral center (C-4 of the nicotinamide ring) are easily distinguished in the region of 2.6 to 2.7 ppm. We found that with the partially purified dehydrogenases (i) 2H from the (2R) center of per-(1S,2R)-benzoate-1,2-dihydrodiol was donated to the Si-face of NAD to give (4S)-NAD2H; (ii) p-toluate-2,3-diol dehydrogenase also provided exclusively (4S)-NAD2H, but the 2H was transferred from both the 2- and ...Continue Reading

References

Mar 1, 1977·Journal of Bacteriology·J J DeFrank, D W Ribbons
Jan 1, 1990·Advances in Microbial Physiology·S J Assinder, P A Williams
Jan 1, 1982·Methods in Enzymology·K You
Jul 1, 1981·Proceedings of the National Academy of Sciences of the United States of America·H JörnvallJ Jeffery

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