Pentafluorobenzylation of alkyl and related DNA base adducts facilitates their determination by electrophore detection.
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.
Saha
M
M
Department of Medicinal Chemistry, College of Pharmacy and Allied Health Professions, Northeastern University, Boston, MA.
Minnetian
O
O
Fisher
D
D
Rogers
E
E
Annan
R
R
Kresbach
G
G
Vouros
P
P
Giese
R
R
D000478:Alkylation; D004247:DNA / Q000378:metabolism*; D006868:Hydrolysis; D013058:Mass Spectrometry; D013941:Thymine / Q000031:analogs & derivatives / Q000378:metabolism
C040384:4-ethylthymine; D004247:DNA; D013941:Thymine