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 Lettjournal_title
FEMS microbiology lettersauthors
Dolfing Jdoi
10.1111/j.1574-6968.1998.tb13238.xsubject
Has Abstractpub_date
1998-10-15 00:00:00pages
271-4issue
2eissn
0378-1097issn
1574-6968pii
S0378-1097(98)00399-1journal_volume
167pub_type
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journal_title:FEMS microbiology letters
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