|
|||||
|
|
Synthesis and properties of 2-azidodeoxyadenosine and its incorporation into oligodeoxynucleotides |
|
| Authors: | Takeshi Wada Akira Mochizuki Seiichiro Higashiya Hiroyuki Tsuruoka Shun-ichi Kawahara Masahide Ishikawa Mitsuo Sekine |
| Affiliation: | aDepartment of Life Science, Tokyo Institute of Technology, Nagatsuta, Midoriku, Yokohama 226-8501, Japan |
| Abstract: | 2-Azidodeoxyadenosine (7) was conveniently synthesized from deoxyguanosine (2) by use of a combined reagent of TMSN3–BuONO. The structure of the tautomer of the azido derivative was determined by 1H NMR. Reaction of 7 with iPr2NP(OEt)2 gave an intermediate 10 of the Staudinger reaction. Incorporation of 7 into a DNA 13mer resulted in a significant decrease of the Tm value of the DNA duplex upon hybridization with the complementary strand. The thermal stability was discussed based on the hydrogen bond energy and electrostatic repulsion. |
| Keywords: | |
| 本文献已被 ScienceDirect 等数据库收录！ | |