Hybridization ability and base pair geometry of modified deoxycytidine derivatives having a 4-N-carbamoyl group

Nucleic Acids Res Suppl. 2002:(2):161-2. doi: 10.1093/nass/2.1.161.

Abstract

Modified oligodeoxyribonucleotides incorporating 4-N-carbamoyldeoxycytidine derivatives were synthesized. The 1H-NMR of 4-N-carbamoyldeoxycytidine suggests that the carbamoyl group forms an intramolecular hydrogen bond with the cytosine ring nitrogen atom and this geometry would inhibit formation of the Watson-Crick base pair with a guanine base. However, the Tm analysis of the modified oligodeoxynucleotides revealed that, in the process of their hybridization with the complementary oligodeoxynucleotides, the orientation of the carbamoyl group changed in a manner where the stable Watson-Crick base pair can be formed with the guanine base.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Base Pairing*
  • Deoxycytidine / chemistry*
  • Nucleic Acid Hybridization*

Substances

  • Deoxycytidine