7-Deaza-2,8-diazaadenine containing oligonucleotides: synthesis, ring opening and base pairing of 7-halogenated nucleosides

Autor(en): Lin, WQ
Xu, KY
Seela, F
Stichwörter: 2-AZA-2'-DEOXYADENOSINE; 2-AZAPURINES; 7-DEAZAPURINE; ANALOGS; azapurine; base pairing; Chemistry; Chemistry, Organic; DERIVATIVES; DNA; DUPLEX STABILITY; GLYCOSYLATION; IMIDAZOLE NUCLEOSIDES; nucleosides; oligonucleotides; PURINE; pyrazole
Erscheinungsdatum: 2005
Herausgeber: PERGAMON-ELSEVIER SCIENCE LTD
Journal: TETRAHEDRON
Volumen: 61
Ausgabe: 31
Startseite: 7520
Seitenende: 7527
Zusammenfassung: 
Oligonucleotides containing 7-bromo-7-deaza-2,8-diaza-2'-deoxyadenosine (3) and 5-amino-3-bromo-4-carbamoyl-1-(2'-deoxy-beta-D-erythro-pentofuranosyl)py razole (4) were synthesized. Compound 3 was prepared from 7-bromo-8-aza-7-deaza-2'-deoxyadenosine (5) via the 1,N-6-etheno derivative 6 and was converted into the phosphoramidite 11. The 7-bromo substituent of 3 increases oligonucleotide duplex stability compared to the non-halogenated nucleoside. Oligonucleotides incorporating 3 are transformed to those containing 4 during long time deprotection at elevated temperature (25% aq ammonia, 60 degrees C, 30 h). Compound 3 forms a strong base pair with dG. The base pair stability decreases in the order dG > dT > dA > dC. Similar recognition selectivity is observed for the pyrazole nucleoside 4, however, due to decreased stacking and higher flexibility of the pyrazole moiety, duplexes are less stable than those containing 3. (c) 2005 Elsevier Ltd. All rights reserved.
ISSN: 00404020
DOI: 10.1016/j.tet.2005.05.046

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