Photoaddition of 4,6-dimethyltetrahydrobenzoangelicin to thymine in DNA: X-ray studies and experiments with model oligonucleotides.
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.
Caffieri
S
S
Department of Pharmaceutical Sciences, University of Padova, Italy. caffieri@dsfarm.unipd.it
Miolo
G
G
Dall'Acqua
F
F
Benetollo
F
F
Bombieri
G
G
D001483:Base Sequence; D001665:Binding Sites; D004247:DNA / Q000737:chemistry* / Q000528:radiation effects*; D011564:Furocoumarins / Q000737:chemistry* / Q000528:radiation effects*; D066298:In Vitro Techniques; D009838:Oligodeoxyribonucleotides / Q000737:chemistry / Q000528:radiation effects; D010777:Photochemistry; D013941:Thymine / Q000737:chemistry / Q000528:radiation effects
D011564:Furocoumarins; D009838:Oligodeoxyribonucleotides; C059470:tetrahydrobenzo-4,6-dimethylangelicin; D004247:DNA; D013941:Thymine