T. Wada, Akira Mochizuki, S. Higashiya
Dec 24, 2001
Citations
0
Influential Citations
43
Citations
Journal
Tetrahedron Letters
Abstract
Abstract 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 i Pr 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.