DNA photo-cross-linking using 3-cyanovinylcarbazole modified oligonucleotide with threoninol linker

Org Lett. 2015 Feb 20;17(4):936-9. doi: 10.1021/acs.orglett.5b00035. Epub 2015 Feb 5.

Abstract

3-Cyanovinylcarbazole modified D-threoninol ((CNV)D) was incorporated in oligodeoxyribonucleotide and tested for a photo-cross-linking reaction with complementary oligodeoxyribonucleotide. The photoreactivity was 1.8- to 8-fold greater than that of 3-cyanovinylcarbazole modified deoxyribose ((CNV)K) previously reported. From the results of melting analysis and circular dichroism spectroscopy of the duplexes, the relatively flexible structure of (CNV)D compared with (CNV)K might be advantageous for [2 + 2] photocycloaddition between the cyanovinyl group on the (CNV)D and pyrimidine base in the complementary strand.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Alcohols / chemistry*
  • Butylene Glycols / chemistry*
  • Carbazoles / chemistry*
  • Cross-Linking Reagents / chemistry*
  • DNA / chemistry*
  • Molecular Structure
  • Oligodeoxyribonucleotides / chemistry*
  • Photochemical Processes
  • Pyrimidines / chemistry

Substances

  • Amino Alcohols
  • Butylene Glycols
  • Carbazoles
  • Cross-Linking Reagents
  • Oligodeoxyribonucleotides
  • Pyrimidines
  • threoninol
  • DNA
  • pyrimidine