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Photoaddition of 4,6‐Dimethyltetrahydrobenzoangelicin to Thymine in DNA: X‐ray Studies and Experiments with Model Oligonucleotides ¶
Author(s) -
Caffieri Sergio,
Miolo Giorgia,
Dall'Acqua Francesco,
Benetollo Franco,
Bombieri Gabriella
Publication year - 2000
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1562/0031-8655(2000)0720023podtti2.0.co2
Subject(s) - psoralen , furocoumarin , oligonucleotide , thymine , furan , chemistry , dna , stereochemistry , sequence (biology) , enantiomer , crystal structure , crystallography , x ray , organic chemistry , biochemistry , physics , quantum mechanics
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.