Separate deamination mechanisms for isomeric styrene oxide induced N1-adenine adducts.
[formula: see text] Styrene 7,8-oxide (SO) induced N1-2'-deoxyadenosine 5'-phosphate (AMP) adducts deaminate to corresponding inosine derivatives. For the beta-isomer of N1-SO-AMP, the chiral alpha-carbon was found to be involved in the hydrolytic deamination, suggesting formation of an oxazolinium ring as an intermediate and that a water molecule attacks the benzylic carbon. The mechanism differs from the one suggested for the alpha-isomer of N1-SO-AMP, for which deamination occurs by direct attack of water at the 6-position of purine ring.
Koskinen
M
M
Department of Biosciences, Novum, Karolinska Institute, Huddinge, Sweden. mikko.koskinen@cnt.ki.se
Hemminki
K
K
D000225:Adenine / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D003641:Deamination; D004852:Epoxy Compounds / Q000737:chemistry / Q000494:pharmacology*; D007536:Isomerism; D013058:Mass Spectrometry; D013056:Spectrophotometry, Ultraviolet
D004852:Epoxy Compounds; C013690:styrene oxide; D000225:Adenine