Pyrazolo[3,4-d][1,2,3]triazine DNA: Synthesis and Base Pairing of 7-Deaza-2,8-diaza-2‘-deoxyadenosine
- 17 June 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (14) , 4695-4700
- https://doi.org/10.1021/jo040150i
Abstract
7-Deaza-2,8-diaza-2‘-deoxyadenosine (4) was synthesized from 8-aza-7-deaza-2‘-deoxyadenosine (1) via the 1,N6-etheno derivative 5. Ring opening with sodium hydroxide followed by ring closure in the presence of sodium nitrite formed the tricyclic intermediate 5 from which the transiently introduced “etheno” moiety was removed with NBS. Compound 4 was converted to the phosphoramidite 11, which was employed in solid-phase oligonucleotide synthesis. Base pairing studies on 4, incorporated in a 12-mer duplex, showed that this adenine nucleoside analogue forms a strong base pair with dG but not with dT. This novel base pair is as stable as that of the canonical dA-dT pair. As a result of the absence of nitrogen-7 compound 4 is expected to form a face to face base pair with dG.Keywords
This publication has 30 references indexed in Scilit:
- Synthesis and Biophysical and Biological Properties of Oligonucleotides Containing 2-Aza-2'-DeoxyinosineThe Journal of Organic Chemistry, 1995
- Solution Structure of a GA Mismatch DNA Sequence, d(CCATGAATGG)2, Determined by 2D NMR and Structural Refinement MethodsBiochemistry, 1994
- Facile Synthesis of 2′‐Deoxyribofuranosides of Allopurinol and 4‐Amino‐1H‐pyrazolo[3,4‐d]pyrimidine via Phase‐Transfer GlycosylationHelvetica Chimica Acta, 1985
- Synthesis of 8-methyl-2-azainosine and related nucleosidesJournal of Heterocyclic Chemistry, 1984
- Synthesis and biological evaluation of 2-fluoro-8-azaadenosine and related compoundsJournal of Medicinal Chemistry, 1983
- Nucléosides de synthèse XXI. Obtention spécifique de ribonucléosides de configuration anomérique αJournal of Heterocyclic Chemistry, 1982
- Acyclic analogues of purine and imidazole nucleosidesJournal of Heterocyclic Chemistry, 1982
- Synthesis of 2-substituted derivatives of 5-amino-1-.beta.-D-ribofuranosylimidazole-4-carboxamide. Ring opening reactions of 2-azapurine nucleosidesThe Journal of Organic Chemistry, 1974
- Transformations in the morphine series. 5. Reaction of codeinone with dimethyloxosulfonium methylide. Structure and analgetic activity of the product and its reduced formJournal of Medicinal Chemistry, 1972
- The synthesis of 2‐azainosine and related derivatives by ring annulation of imidazole nucleosidesJournal of Heterocyclic Chemistry, 1972