Halogenation of aromatic compounds: thermodynamic, mechanistic and ecological aspects.

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 O2 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 O2 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 O2 as the oxidant.

journal_name

FEMS Microbiol Lett

authors

Dolfing J

doi

10.1111/j.1574-6968.1998.tb13238.x

subject

Has Abstract

pub_date

1998-10-15 00:00:00

pages

271-4

issue

2

eissn

0378-1097

issn

1574-6968

pii

S0378-1097(98)00399-1

journal_volume

167

pub_type

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