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Analysis of institutional authors

Fernandez Pacios, LuisAuthorMerino, IreneAuthorGomez, LuisCorresponding Author

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June 9, 2019
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Structures and Thermodynamics of Biphenyl Dihydrodiol Stereoisomers and Their Metabolites in the Enzymatic Degradation of Arene Xenobiotics

Publicated to: Journal Of Computational Chemistry. 30 (15): 2420-2432 - 2009-11-30 30(15), DOI: 10.1002/jcc.21248

Authors:

Pacios, Luis F; Campos, Victor M; Merino, Irene; Gomez, Luis
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Affiliations

Univ Politecn Madrid, Dept Biotecnol, Unidad Quim & Bioquim, ETS Ingenieros Montes, E-28040 Madrid, Spain - Author

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 (hydroxy-ketones, II), as well as final catechol (2,3-biphenyidiol, 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 (Delta H-R(0) similar to 1.5-4 kcal mol(-1)) and exergonic (Delta G(R)(0) similar to -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 (Delta H-R(0) similar to -27, Delta G(R)(0) similar to -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. (C) 2009 Wiley Periodicals, Inc. J Comput Chem 30: 2420-2432, 2009
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Keywords

2,2'-dipyridylAb initio calculationsAb-initioBiodegradation of xenobioticsBiphenylCalixarenesCatecholCatecholsChemoenzymatic synthesisComputer simulationCrystal-structureDihydrodiolsDioxygenasesElectron-densityHydrogen-bond dimersModels, chemicalMolecular structureMonosubstituted benzenesNaphthalenesPolychlorinated-biphenylsPolycyclic aromatic-hydrocarbonsPseudomonas strain lb400Quantum theoryShort-chain dehydrogenases/reductasesStereoisomerismThermochemistry of stereoisomersThermodynamicsTrans-1,2-dihydro-1,2-naphthalenediolXenobiotics

Quality index

Bibliometric impact. Analysis of the contribution and dissemination channel

The work has been published in the journal Journal Of Computational Chemistry due to its progression and the good impact it has achieved in recent years, according to the agency WoS (JCR), it has become a reference in its field. In the year of publication of the work, 2009, it was in position 26/138, thus managing to position itself as a Q1 (Primer Cuartil), in the category Chemistry, Multidisciplinary.

Independientemente del impacto esperado determinado por el canal de difusión, es importante destacar el impacto real observado de la propia aportación.

Según las diferentes agencias de indexación, el número de citas acumuladas por esta publicación hasta la fecha 2026-01-20:

  • WoS: 1
  • Scopus: 1
  • Europe PMC: 1
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Impact and social visibility

From the perspective of influence or social adoption, and based on metrics associated with mentions and interactions provided by agencies specializing in calculating the so-called "Alternative or Social Metrics," we can highlight as of 2026-01-20:

  • The use of this contribution in bookmarks, code forks, additions to favorite lists for recurrent reading, as well as general views, indicates that someone is using the publication as a basis for their current work. This may be a notable indicator of future more formal and academic citations. This claim is supported by the result of the "Capture" indicator, which yields a total of: 8 (PlumX).
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Leadership analysis of institutional authors

There is a significant leadership presence as some of the institution’s authors appear as the first or last signer, detailed as follows: First Author (Pacios, Luis F.) and Last Author (GOMEZ FERNANDEZ, LUIS).

the authors responsible for correspondence tasks have been Pacios, Luis F. and GOMEZ FERNANDEZ, LUIS.

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Awards linked to the item

Contract/grant sponsor: Comunidad de Madrid, Spain; contract/grant numbers: EIADES, S-0505/AMB/0296
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