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Model quantum‐chemical studies on the reaction between the candidate proximate carcinogen benzo(a)pyrene‐7,8‐dihydrodiol‐9,10‐epoxide and guanine
Author(s) -
Lavery Richard,
Pullman Alberte,
Pullman Bernard
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.560140707
Subject(s) - carbonium ion , chemistry , guanine , epoxide , benzo(a)pyrene , adduct , electrophile , deprotonation , nucleic acid , pyrene , diol , reaction mechanism , carcinogen , stereochemistry , organic chemistry , nucleotide , biochemistry , ion , gene , catalysis
Abstract Recent experimental evidence has pointed to “bay‐region” diol epoxides as possible proximate metabolites for a range of polycyclic aromatic hydrocarbons that form adducts with the bases of cellular nucleic acids. The authors present a theoretical model study of a possible reaction mechanism to produce such adducts. This mechanism consists of an electrophilic substitution on the NH 2 group of guanine by a carbonium ion derived from the opening of the epoxide. It involves the formation of a quaternary intermediate followed by an OH − assisted deprotonation. The easy deformability of the NH 2 group of the base plays an important role in the evolution of the reaction.