Photoaddition of 4,6-dimethyltetrahydrobenzoangelicin to thymine in DNA: X-ray studies and experiments with model oligonucleotides

Photochem Photobiol. 2000 Jul;72(1):23-7. doi: 10.1562/0031-8655(2000)072<0023:podtti>2.0.co;2.

Abstract

The crystal structures of 4,6-dimethyltetrahydrobenzoangelicin (THBA), a furocoumarin analog, and of its furan-side cis-syn cycloadduct with thymine formed in the photoreaction with DNA, have been determined. The crystal structure of the latter compound contained only one enantiomeric form corresponding to the addition to a 5'-XpT site. Contrary to most psoralen derivatives studied, THBA showed higher photoreactivity toward synthetic oligonucleotides containing that sequence than toward those with the 5'-TpX sequence.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Base Sequence
  • Binding Sites
  • DNA / chemistry*
  • DNA / radiation effects*
  • Furocoumarins / chemistry*
  • Furocoumarins / radiation effects*
  • In Vitro Techniques
  • Oligodeoxyribonucleotides / chemistry
  • Oligodeoxyribonucleotides / radiation effects
  • Photochemistry
  • Thymine / chemistry
  • Thymine / radiation effects

Substances

  • Furocoumarins
  • Oligodeoxyribonucleotides
  • tetrahydrobenzo-4,6-dimethylangelicin
  • DNA
  • Thymine