1997
DOI: 10.1128/jb.179.12.4023-4029.1997
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Stereochemical course of two arene-cis-diol dehydrogenases specifically induced in Pseudomonas putida

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. H was transferred from both the 2-and 3-C atoms of (2S,3R)-p-toluate-2,3-dihydrodiol with specifically deuterated species in approximately equal amounts; and (iii) the unexpected lack of stereo-and regioselectivity of p-toluate-2,3-dio… Show more

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Cited by 14 publications
(11 citation statements)
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“…Thus, a similar conclusion was reached by Ribbons et al [28] when using 1-D-toluene-cis-1,2-dihydrodiol B (R = Me) as substrate for toluene-cis-2,3-dihydrodiol dehydrogenase (TDD) as biocatalyst from P. putida F1. TDD-catalysed the exclusive transfer of the deuterium atom from position C-1 to NAD during formation of 3-methylcatechol C (R = Me).…”
supporting
confidence: 64%
“…Thus, a similar conclusion was reached by Ribbons et al [28] when using 1-D-toluene-cis-1,2-dihydrodiol B (R = Me) as substrate for toluene-cis-2,3-dihydrodiol dehydrogenase (TDD) as biocatalyst from P. putida F1. TDD-catalysed the exclusive transfer of the deuterium atom from position C-1 to NAD during formation of 3-methylcatechol C (R = Me).…”
supporting
confidence: 64%
“…In both cases, carbonyl is formed at C3, a result supported by different deuterium labeling studies on dihydrodiols resulting from naphthalene41 and several monocyclic arenes48 that have established that oxidation of the OH group is preferred to occur at position C3.…”
Section: Results and Analysismentioning
confidence: 79%
“…In this reaction, tetravalent positive N atom changes to trivalent neutral N atom and the aromatic C‐ 4 atom becomes tetrahedral. The well established stereospecificity of NAD+ enzymes48, 49 implies that in their reverse action on carbonyl substrates, the H atom donated is just that drawn below nicotinamide ring in Figure 6 and not the one depicted above. In other words, the spatial location of dihydrodiols must fit the inner protein space so as to orient properly with respect to the nicotinamide ring, which in turn is constrained by coenzyme‐binding site geometry.…”
Section: Results and Analysismentioning
confidence: 99%
“…2B) is consistent with a keto hydroxy compound that would arise if the dihydrodiol product 1 were acted on by dihydrodiol dehydrogenase. Note that diol dehydrogenases have previously been shown to act as alcohol dehydrogenases to produce keto alcohols, which isomerize with rearomation to a catechol in the case of keto alcohols of cyclohexadienes (9). With an oxidation series for cyclopentadiene ring compounds similar to that found in compound 1, a keto alcohol would not isomerize, and so this would be the stable structure.…”
Section: Frac Water Ring Compounds Testedmentioning
confidence: 99%