Model quantum-chemical studies on the reaction between the candidate proximate carcinogen benzo(a)pyrene-7,8-dihydrodiol-9,10-epoxide and guanine

Autor:	Richard Lavery, Bernard Pullman, Alberte Pullman
Rok vydání:	2009
Předmět:	Reaction mechanism Stereochemistry Guanine Epoxide Condensed Matter Physics Atomic and Molecular Physics and Optics Adduct chemistry.chemical_compound Electrophilic substitution Deprotonation chemistry Benzo(a)pyrene Carbonium ion Physical and Theoretical Chemistry
Zdroj:	ResearcherID
ISSN:	1097-461X 0020-7608
Popis:	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 NH2 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 NH2 group of the base plays an important role in the evolution of the reaction.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::7e9464e2e3a678d0dea48389e5c940ce https://doi.org/10.1002/qua.560140707 Zobrazit plný text záznamu Plný text