Stability of 7-alkyldeoxyguanosines of trichloropropylene oxide, epichlorohydrin and glycidol.
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).
D000478:Alkylation; D003849:Deoxyguanosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D004355:Drug Stability; D006863:Hydrogen-Ion Concentration
C049088:7-(2,3-dihydroxypropane)deoxyguanosine; C049086:7-(3-trichloro-2-hydroxypropane)deoxyguanosine; C049087:7-(3-chloro-2-hydroxypropane)deoxyguanosine; D003849:Deoxyguanosine