Chemical synthesis and properties of (6-4) photoproduct and its analogs

Nucleic Acids Symp Ser. 1999:(42):37-8. doi: 10.1093/nass/42.1.37.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antibodies
  • DNA / chemistry
  • DNA / radiation effects*
  • DNA Damage*
  • Indicators and Reagents
  • Models, Molecular
  • Molecular Conformation
  • Pyrimidine Dimers / chemical synthesis*
  • Pyrimidine Dimers / chemistry*
  • Ultraviolet Rays

Substances

  • Antibodies
  • Indicators and Reagents
  • Pyrimidine Dimers
  • DNA