Hybridization ability and base pair geometry of modified deoxycytidine derivatives having a 4-N-carbamoyl group.
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.
Miyata
Kenichi
K
Department of Life Science, Tokyo Institute of Technology, 4259 Nagatsutacyo, Midoriku, Yokohama 226-8501, Japan.
Kobori
Akio
A
Seio
Kohji
K
Sekine
Mitsuo
M
D020029:Base Pairing; D003841:Deoxycytidine / Q000737:chemistry*; D009693:Nucleic Acid Hybridization
D003841:Deoxycytidine