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Substrate and Enzyme Specificity of the Kinetic Isotope Effects Associated with the Dioxygenation of Nitroaromatic Contaminants
Eawag, Swiss Fed Inst Aquat Sci & Technol, CH-8600 Dubendorf, Switzerland.;Swiss Fed Inst Technol, Inst Biogeochem & Pollutant Dynam IBP, CH-8092 Zurich, Switzerland..
Eawag, Swiss Fed Inst Aquat Sci & Technol, CH-8600 Dubendorf, Switzerland..
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Biologiska sektionen, Institutionen för cell- och molekylärbiologi, Struktur- och molekylärbiologi. Lodz Univ Technol, Inst Appl Radiat Chem, PL-90924 Lodz, Poland..
Lodz Univ Technol, Inst Appl Radiat Chem, PL-90924 Lodz, Poland..
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2016 (engelsk)Inngår i: Environmental Science and Technology, ISSN 0013-936X, E-ISSN 1520-5851, Vol. 50, nr 13, s. 6708-6716Artikkel i tidsskrift (Fagfellevurdert) Published
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Abstract [en]

Compound-specific isotope analysis (CSIA) is a promising approach for tracking biotransformation of organic pollutants, but isotope fractionation associated with aromatic oxygenations is only poorly understood. We investigated the dioxygenation of a series of nitroaromatic compounds to the corresponding catechols by two enzymes, namely, nitrobenzene and 2-nitrotoluene dioxygenase (NBDO and 2NTDO) to elucidate the enzyme- and substrate-specificity of C and H isotope fractionation. While the apparent C-13- and H-2-kinetic isotope effects of nitrobenzene, nitrotoluene isomers, 2,6-dinitrotoluene, and naphthalene dioxygenation by NBDO varied considerably, the correlation of C and H isotope fractionation revealed a common mechanism for nitrobenzene and nitrotoluenes. Similar observations were made for the dioxygenation of these substrates by 2NTDO. Evaluation of reaction kinetics, isotope effects, and commitment-to-catalysis based on experiment and theory showed that rates of dioxygenation are determined by the enzymatic O-2 activation and aromatic C oxygenation. The contribution of enzymatic O-2 activation to the reaction rate varies for different nitroaromatic substrates of NBDO and 2NTDO. Because aromatic dioxygenation by nonheme iron dioxygenases is frequently the initial step of biodegradation, O-2 activation kinetics may also have been responsible for the minor isotope fractionation reported for the oxygenation of other aromatic contaminants.

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2016. Vol. 50, nr 13, s. 6708-6716
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URN: urn:nbn:se:uu:diva-300468DOI: 10.1021/acs.est.5b05084ISI: 000379366300016PubMedID: 26895026OAI: oai:DiVA.org:uu-300468DiVA, id: diva2:951447
Tilgjengelig fra: 2016-08-09 Laget: 2016-08-09 Sist oppdatert: 2017-11-28bibliografisk kontrollert

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