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A theoretical investigation of the first step in the metabolic reduction of halogenated methanes by cytochrome P‐450
Author(s) -
Luke Brian T.,
Loew Gilda H.
Publication year - 2009
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.560280711
Subject(s) - chemistry , substrate (aquarium) , mndo , cytochrome , computational chemistry , active site , stereochemistry , enzyme , electron affinity (data page) , reduction (mathematics) , organic chemistry , molecule , oceanography , geology , geometry , mathematics
The first step in the anaerobic reduction of halogenated hydrocarbons by cytochrome P–450 is the Abstraction of an electron from the reduced enzyme by the substrate located in a lipophilic binding site. To determine which halogenated hydrocarbons might be active substrates for this reductive metabolism, the vertical electron affinity of a number of bromo‐ and iodohalomethanes has been calculated using the MNDO method. Combining these results with earlier calculations on the fluoro‐ and chlorohalomethanes, and examining the available experimental evidence, yields the prediction that among the chloro‐ and fluoromethanes, only CF 2 Cl 2 , CHCl 3 , CFCl 3 , and CCl 4 could be active substrates. Similarly, all bromohalomethanes, with the exception of CH 3 Br, CH 2 FBr, and CHF 2 Br, are predicted to be active substrates, as are all iodohalomethanes, including CH 3 I.