Reaction kinetics of alkyl epoxides with DNA and other nucleophiles.
1,2-Epoxy alkanes from C3 to C8 were reacted with DNA, deoxyguanosine and 4-(p-nitrobenzyl) pyridine (NBP). DNA was hydrolyzed at neutral pH to release 7-alkylguanines. The products were analyzed by HPLC. The epoxides reacted largely according to the chain length, shorter epoxides being more reactive. Substitutions through carbon 1 predominated. Reactivity with NBP was almost equal between the epoxides.
Hemminki
A
A
Center for Nutrition and Toxicology, Karolinska Institute, Novum, Huddinge, Sweden.
Väyrynen
T
T
Hemminki
K
K
D000473:Alkanes / Q000737:chemistry*; D002863:Chromogenic Compounds; D004247:DNA / Q000737:chemistry*; D003849:Deoxyguanosine / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D007700:Kinetics; D011725:Pyridines / Q000737:chemistry*; D013329:Structure-Activity Relationship
D000473:Alkanes; D002863:Chromogenic Compounds; D004852:Epoxy Compounds; D011725:Pyridines; C008633:4-(4-nitrobenzyl)pyridine; D004247:DNA; D003849:Deoxyguanosine