8-azaadenosine and its 2 `-deoxyribonucleoside: Synthesis and oligonucleotide base-pair stability

Autor(en): Seela, F
Munster, I
Lochner, U
Rosemeyer, H 
Stichwörter: 2',3'-DIDEOXYRIBONUCLEOSIDES; 2',5'-OLIGOADENYLATES; 2',5'-OLIGONUCLEOTIDE ANALOGS; 2'-DEOXYRIBOFURANOSIDES; 8-AZA-2'-DEOXYGUANOSINE; Chemistry; Chemistry, Multidisciplinary; DEOXYNUCLEOSIDES; DNA; GLYCOSYLATION; HYBRIDIZATION; NUCLEOSIDES
Erscheinungsdatum: 1998
Herausgeber: WILEY-V C H VERLAG GMBH
Journal: HELVETICA CHIMICA ACTA
Volumen: 81
Ausgabe: 6
Startseite: 1139
Seitenende: 1155
Zusammenfassung: 
The synthesis of 8-azaadenosine (1a; z(8)A) has been performed by SnCl4-catalyzed glycosylation of 8-azaadenine (4) with 1,2,3,5-tetra-O-acetyl-beta-D-ribofuranose (5), followed by the separation of the regioisomers 6 and 7 and subsequent deacetylation. The ribonucleoside 1a as well as its 2'-deoxy derivative 1b (z(8)A(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 (z(8)A-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.
ISSN: 0018019X
DOI: 10.1002/hlca.19980810527

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