Distinct conformers of alkylchrysene diol epoxide-deoxyguanosine adducts detected by proton NMR

Chem Res Toxicol. 1992 Nov-Dec;5(6):756-9. doi: 10.1021/tx00030a004.

Abstract

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.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Carcinogens / chemistry*
  • Chromatography, High Pressure Liquid
  • Chrysenes / chemistry*
  • DNA Damage*
  • Deoxyguanosine / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation

Substances

  • Carcinogens
  • Chrysenes
  • 1,2-dihydroxy-epoxy-1,2,3,4-tetrahydro-5-methylchrysene
  • Deoxyguanosine