2-aza-2'-deoxyadenosine: synthesis, base-pairing selectivity, and stacking properties of oligonucleotides

Chemistry : a European Journal
T SugiyamaFrank Seela

Abstract

2-Aza-2'-deoxyadenosine (2, z2Ad) is synthesized via its 1,N6-etheno derivative 7 and enzymatically deaminated to 2-aza-2'-deoxyinosine (3). Compound 2 is converted into the phosphoramidite building block 10b. This is employed in solid-phase oligonucleotide synthesis. The 2-azapurine base forms a strong base pair with guanine, but a much weaker one with adenine, thymine, and cytosine. Oligonucleotide duplexes with dangling nucleotide residues, such as 2-aza-2'-deoxyadenosine and 7-deaza-2'-deoxyadenosine (4, c7Ad), either on one or both termini, are synthesized, and the thermal stability of the duplexes is correlated with the hydrophobic properties of the dangling nucleotide residues.

Citations

Nov 4, 2009·Chemical Research in Toxicology·Uthpala SeneviratneNatalia Tretyakova
Nov 17, 2007·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Mariusz MojzychJacek Wierzchowski
Sep 23, 2010·Chemistry & Biodiversity·Simone Budow, Frank Seela
Dec 24, 2005·Chemical Communications : Chem Comm·Young Jun Seo, Byeang Hyean Kim
Oct 21, 2000·Biochemistry·K VastmansP Herdewijn
Jul 3, 2004·The Journal of Organic Chemistry·Frank SeelaWenqing Lin
Jul 9, 2021·The Journal of Physical Chemistry. B·Robert J FickAllison L Stelling

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