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Halogenation of aromatic compounds: thermodynamic, mechanistic and ecological aspects

Lookup NU author(s): Dr Jan Dolfing

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Abstract

Biological halogenation of aromatic compounds implies the generation of reducing equivalents in the form of e.g. NADH. Thermodynamic calculations show that coupling the halogenation step to a step in which the reducing equivalents are oxidized with a potent oxidant such as O-2 or N2O makes the halogenation reaction thermodynamically feasible without the input of additional energy in the form of e.g. NADH. In a current model on the halogenation of tryptophan to 7-chloro-L-tryptophan NADH and O-2 are proposed as co-substrates in a reaction in which the aromatic compound is oxidized via an epoxide as intermediate. The thermodynamic calculations thus indicate that such a route hinges on mechanistic insights but has no thermodynamic necessity. Furthermore the calculations suggest that halogenation of tryptophan and other aromatic compounds should be possible with N2O, and possibly even with nitrate replacing O-2 as the oxidant. (C) 1998 Federation of European Microbiological Societies. Published by Elsevier Science B.V. All rights reserved.


Publication metadata

Author(s): Dolfing J

Publication type: Article

Publication status: Published

Journal: FEMS Microbiology Letters

Year: 1998

Volume: 167

Issue: 2

Pages: 271-274

Print publication date: 15/10/1998

ISSN (print): 0378-1097

ISSN (electronic): 1574-6968

URL: http://dx.doi.org/10.1111/j.1574-6968.1998.tb13238.x

DOI: 10.1111/j.1574-6968.1998.tb13238.x

Notes: Times Cited: 3 Cited Reference Count: 18 English Article FEMS MICROBIOL LETT 132BY


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