Distinct conformers of alkylchrysene diol epoxide-deoxyguanosine adducts detected by proton NMR.
Proton NMR spectra, obtained in MeOH-d4, of the major DNA adduct of 5,7-dimethylchrysene-1,2-diol 3,4-epoxide, identified as 1(R),2(S),3(S)-trihydroxy-4(S)-(N2-deoxyguanosyl)-1, 2,3,4-tetrahydro-5,7-dimethylchrysene, showed the presence of two distinct conformers. One conformer, similar to those observed previously in spectra of peracetates of related DNA adducts of anti-diol epoxides of polynuclear aromatic hydrocarbons, had a chair-like conformation of the tetrahydrobenzo ring. The other conformer, which has not been previously observed, had a boat-like conformation of the tetrahydrobenzo ring. This conformer was converted to the chair-like conformer upon addition of D2O or trifluoroacetic acid to the MeOH-d4 solutions of the adduct. The new conformers were also observed in proton NMR spectra of major DNA adducts of 5-methylchrysene- and 5,6-dimethylchrysene-1,2-diol 3,4-epoxides.
Misra
B
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Division of Chemical Carcinogenesis, American Health Foundation, Valhalla, New York 10595.
Lin
J M
JM
Amin
S
S
Hecht
S S
SS
D002273:Carcinogens / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D002911:Chrysenes / Q000737:chemistry*; D004249:DNA Damage; D003849:Deoxyguanosine / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation
D002273:Carcinogens; D002911:Chrysenes; C037783:1,2-dihydroxy-epoxy-1,2,3,4-tetrahydro-5-methylchrysene; D003849:Deoxyguanosine