Helvetica Chimica Acta p. 1139 - 1155 (1998)
Update date:2022-08-04
Topics:
Seela
Munster
Lochner
Rosemeyer
The synthesis of 8-azaadenosine (1a; z8A) has been performed by SnCl4- catalyzed glycosylation of 8-azaadenine (4) with 1,2,3,5-tetra-O-acetyl-β- D-ribofuranose (5), followed by the separation of the regioisomers 6 an d7 and subsequent deacetylation. The ribonucleoside 1a as well as its 2'-deoxy derivative 1b (z8A(d)) were converted into oligonucleotide building blocks- the phosphonate 2 as well as the phosphoramidites 3 and 19. They were used to prepare the oligoribonucleotide (z8A-U)6 and oligodeoxyribonucleotides. The T(m) values and the thermodynamic data of duplex formation of the modified duplexes showed no significant changes compared to those containing A(d) or A residues. This indicates that the stereoelectronic effect of the 8-azaadenine base which was found for the monomeric nucleoside has only a minor influence on the duplex stability.
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Doi:10.1016/S0014-827X(98)00005-6
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