title: Stability of 7-alkyldeoxyguanosines of trichloropropylene oxide, epichlorohydrin and glycidol.
abstract: Deoxyguanosine was reacted with trichloropropylene oxide (TCPO), epichlorohydrin and glycidol in aqueous solution and the products were isolated by high pressure liquid chromatography (HPLC). For each compound 7-alkyldeoxyguanosine was the main adduct; TPCO reacted about 3 times faster than epichlorohydrin and about 10 times faster than glycidol. The pKa's of the 7-alkyldeoxyguanosines were 6.7, 6.8 and 6.9 for the TCPO-, epichlorohydrin-, and glycidol-adducts, respectively. The respective half-lives of imidazole ring-opening were 6.3, 15 and 27 hrs (pH 8.5, 28 degrees) and those of depurination 1.9, 3.4 and 4.4 hrs (pH 5.5, 28 degrees).
mesh_terms: D000478:Alkylation; D003849:Deoxyguanosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D004355:Drug Stability; D006863:Hydrogen-Ion Concentration
chemical_list: C049088:7-(2,3-dihydroxypropane)deoxyguanosine; C049086:7-(3-trichloro-2-hydroxypropane)deoxyguanosine; C049087:7-(3-chloro-2-hydroxypropane)deoxyguanosine; D003849:Deoxyguanosine