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- W2142227251 abstract "A key step in the metabolic degradation of biphenyl xenobiotics is catechol formation upon dehydrogenation of cis- and trans-dihydrodiols in prokaryotic and eukaryotic pathways, respectively. Structure and thermodynamics of stereoisomers of cis-, trans-2,3-biphenyl-dihydrodiols (I) and their dehydrogenation products (hydroxyketones, II), as well as final catechol (2,3-biphenyldiol, III) are studied by means of ab initio MP2/6-311++G(2df,2p)//MP2/6-311G(d,p) calculations. Formation of stereoisomers I and II is exothermic and endergonic, whereas III is enthalpically and entropically driven. Dehydrogenations are endothermic (ΔH ∼ 1.5–4 kcal mol−1) and exergonic (ΔG ∼ −5 to −7.5 kcal mol−1) without noticeable differences between cis and trans pathways, although the same keto stereoisomer II-(2S) is found to be the more favored product from both cis- and trans-I. The final II → III tautomerization is thermodynamically enhanced (ΔH ∼ −27, ΔG ∼ −28 kcal mol−1) but the process is shown to have a large activation energy if it had to occur via unimolecular path. Although this tautomerization is generally assumed to be a nonenzymatic process as it involves rearomatization of an oxygenated ring, proton transfer with an anionic intermediate might be a more probable process. © 2009 Wiley Periodicals, Inc. J Comput Chem, 2009" @default.
- W2142227251 created "2016-06-24" @default.
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- W2142227251 creator A5031514818 @default.
- W2142227251 date "2009-11-30" @default.
- W2142227251 modified "2023-10-01" @default.
- W2142227251 title "Structures and thermodynamics of biphenyl dihydrodiol stereoisomers and their metabolites in the enzymatic degradation of arene xenobiotics" @default.
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