Pyrazolo[3,4-d][1,2,3]triazine DNA: synthesis and base pairing of 7-deaza-2,8-diaza-2'-deoxyadenosine

The Journal of Organic Chemistry
F SeelaWenqing Lin

Abstract

7-deaza-2,8-diaza-2'-deoxyadenosine (4) was synthesized from 8-aza-7-deaza-2'-deoxyadenosine (1) via the 1,N(6)-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.

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Citations

Aug 12, 2014·European Journal of Medicinal Chemistry·Meng Li, Bao-Xiang Zhao
Sep 23, 2010·Chemistry & Biodiversity·Simone Budow, Frank Seela
Feb 15, 2018·Beilstein Journal of Organic Chemistry·Ranjana Aggarwal, Suresh Kumar
Oct 27, 2005·Nucleosides, Nucleotides & Nucleic Acids·Wenqing LinFrank Seela
Mar 20, 2019·Physical Chemistry Chemical Physics : PCCP·A AbdelazizC Schick

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