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Synthesis and properties of 2-azidodeoxyadenosine and its incorporation into oligodeoxynucleotides

✍ Scribed by Takeshi Wada; Akira Mochizuki; Seiichiro Higashiya; Hiroyuki Tsuruoka; Shun-ichi Kawahara; Masahide Ishikawa; Mitsuo Sekine

Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 124 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)02028-7

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✦ Synopsis

2-Azidodeoxyadenosine (7) was conveniently synthesized from deoxyguanosine (2) by use of a combined reagent of TMSN 3 -BuONO. The structure of the tautomer of the azido derivative was determined by 1 H NMR. Reaction of 7 with iPr 2 NP(OEt) 2 gave an intermediate 10 of the Staudinger reaction. Incorporation of 7 into a DNA 13mer resulted in a significant decrease of the T m 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.

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