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

Autor:	Mitsuo Sekine, Akira Mochizuki, Seiichiro Higashiya, Hiroyuki Tsuruoka, Takeshi Wada, Masahide Ishikawa, Shun-ichi Kawahara
Rok vydání:	2001
Předmět:	Stereochemistry Hydrogen bond Organic Chemistry Biochemistry Tautomer Medicinal chemistry chemistry.chemical_compound chemistry Reagent Drug Discovery Proton NMR Deoxyguanosine A-DNA Staudinger reaction Derivative (chemistry)
Zdroj:	Tetrahedron Letters. 42:9215-9219
ISSN:	0040-4039
DOI:	10.1016/s0040-4039(01)02028-7
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::7bf93165fa48a6ee6e308ac9052bd474 https://doi.org/10.1016/s0040-4039(01)02028-7 Zobrazit plný text záznamu Full Text from ScienceDirect