Chemical synthesis and properties of (6-4) photoproduct and its analogs.
We report the preparation of a deoxyribooligonucleotide containing a new thymine (6-4) photoproduct analog. The (6-4) photoproduct is one of the major forms of DNA lesions, and leads to mutation in DNA. An antibody (64M5) that binds the (6-4) photoproduct has been described. To investigate the interaction of the photoproduct with the 64M5 antibody, we prepared a (6-4) photoproduct analog in which the two thymines were connected with a formacetal linkage. With UV-irradiation, the thymine dimer with the formacetal linkage reacted to the (6-4) photoproduct faster than the phosphodiesterified dimer, and the yields of the analog was higher than those of the natural thymine dimer. The 64M5 antibody exhibited sufficient binding to a tetranucleotide containing the (6-4) photoproduct analog with a formacetal linkage, although the association constant was slightly lower than that for the natural lesion. This (6-4) photoproduct analog may be useful for investigation of other proteins that recognize the (6-4) photoproduct.
Sato
K
K
Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan.
Komatsu
Y
Y
Torizawa
T
T
Kato
K
K
Shimada
I
I
Ohtsuka
E
E
D000906:Antibodies; D004247:DNA / Q000737:chemistry / Q000528:radiation effects*; D004249:DNA Damage; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D011740:Pyrimidine Dimers / Q000138:chemical synthesis* / Q000737:chemistry*; D014466:Ultraviolet Rays
D000906:Antibodies; D007202:Indicators and Reagents; D011740:Pyrimidine Dimers; D004247:DNA