title: Pentafluorobenzylation of alkyl and related DNA base adducts facilitates their determination by electrophore detection.
abstract: The DNA adduct O4-ethylthymine can be alkylated under mild conditions with pentafluorobenzyl bromide. The product has good gas chromatographic characteristics and also forms a structurally characteristic anion in high yield when subjected to electron capture mass spectrometry. Related adducts for other DNA bases behave similarly. These properties stimulated us to develop a general analytical method based on the derivatization reaction. Important for this method is an oxidation-elimination reaction that mildly releases a base from a nucleoside. Thus, a general analytical method based on pentafluorobenzylation is now available for determining many alkyl and related DNA adducts.
authors.affiliation: Department of Medicinal Chemistry, College of Pharmacy and Allied Health Professions, Northeastern University, Boston, MA.
authors.forename: M
authors.initials: M
authors.lastname: Saha
authors.forename: O
authors.initials: O
authors.lastname: Minnetian
authors.forename: D
authors.initials: D
authors.lastname: Fisher
authors.forename: E
authors.initials: E
authors.lastname: Rogers
authors.forename: R
authors.initials: R
authors.lastname: Annan
authors.forename: G
authors.initials: G
authors.lastname: Kresbach
authors.forename: P
authors.initials: P
authors.lastname: Vouros
authors.forename: R
authors.initials: R
authors.lastname: Giese
mesh_terms: D000478:Alkylation; D004247:DNA / Q000378:metabolism*; D006868:Hydrolysis; D013058:Mass Spectrometry; D013941:Thymine / Q000031:analogs & derivatives / Q000378:metabolism
chemical_list: C040384:4-ethylthymine; D004247:DNA; D013941:Thymine