Formation of O6-ethylthioethyldeoxyguanosine from the reaction of chloroethyl ethyl sulfide with deoxyguanosine.
O6-Ethylthioethyldeoxyguanosine has been synthesized from 6-chloro-3',5'-di-O-acetyldeoxyguanosine and characterized by UV, fluorescence, and mass spectrometry. High-pressure liquid chromatography studies have shown that this modified nucleoside is formed when the one-armed sulfur mustard, chloroethyl ethyl sulfide, reacts with deoxyguanosine. This result supports the hypothesis that the mutagenic effects of the sulfur mustards are caused in part by substitution of the O6-position of deoxyguanosine.
D002851:Chromatography, High Pressure Liquid; D003849:Deoxyguanosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D007202:Indicators and Reagents; D013058:Mass Spectrometry; D009150:Mustard Compounds; D009151:Mustard Gas / Q000031:analogs & derivatives*; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet
D007202:Indicators and Reagents; D009150:Mustard Compounds; C031278:2-chloroethyl ethyl sulfide; C043642:O(6)-ethylthioethyldeoxyguanosine; D003849:Deoxyguanosine; D009151:Mustard Gas