PMID: 8600457Mar 1, 1996Paper

Synthesis and characterization of 8-methoxy-2'- deoxyadenosine-containing oligonucleotides to probe the syn glycosidic conformation of 2'-deoxyadenosine within DNA

Nucleic Acids Research
R G EasonS S David

Abstract

The synthesis of 8-methoxy-2'-deoxyadenosine (moA) protected at N6 as an N,N-dimethylformamidine derivative and incorporation of the modified nucleoside into oligodeoxynucleotides via the phosphoramidite method are described. UV thermal denaturation studies were conducted on duplexes containing moA:G, moA:C and moA:T base pairs to determine the thermodynamic stability of duplexes containing moA relative to their adenosine (A)-containing counterparts. In the case of moA:G base pairs the effect of moA substitution is sequence dependent. In A:G mismatch-containing sequences, which have been shown by structural characterization to have a syn conformational preference at the glycosidic bond of A, moA substitution results in stabilization of the duplex. In contrast, in sequences where the A in the A:G mismatch has been shown to prefer the anti conformation moA substitution is destabilizing to the duplex. Thus moA may be a useful probe for investigating the conformational preferences of the N-glycosidic bond of adenosine within DNA. In addition, moA nucleoside is more resistant to acid-catalyzed depurination than previously described 8-bromo-2'-deoxyadenosine, allowing for facile incorporation into oligonucleotides via automated solid...Continue Reading

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Citations

Apr 21, 2004·Journal of Molecular Biology·Hiroyuki KamiyaHideyoshi Harashima
Apr 18, 2003·Bioorganic & Medicinal Chemistry Letters·Lisa S ChenTerry L Sheppard
Mar 23, 2012·Chemistry : a European Journal·Anke DierckxL Marcus Wilhelmsson
Mar 2, 2012·Chembiochem : a European Journal of Chemical Biology·Zita SzombatiChris Meier
Jan 27, 2005·Bioorganic & Medicinal Chemistry·Antonella VirgilioAldo Galeone
Sep 10, 2015·PloS One·Daniel Sylwester BaranowskiAnna Pasternak
Sep 29, 2011·The Journal of Physical Chemistry. B·Andrea L MillenStacey D Wetmore
Jun 10, 2014·Organic & Biomolecular Chemistry·Christopher P LawsonMorten Grøtli
Jun 8, 2001·Nucleosides, Nucleotides & Nucleic Acids·C FàbregaR Eritja
Dec 18, 2002·Nucleosides, Nucleotides & Nucleic Acids·Lisa S Chen, Terry L Sheppard
Oct 27, 2005·Nucleosides, Nucleotides & Nucleic Acids·Antonio RandazzoLuciano Mayol
Mar 6, 2010·The Journal of Physical Chemistry. B·Andrea L MillenStacey D Wetmore
Apr 2, 2008·The Journal of Physical Chemistry. a·Andrea L MillenStacey D Wetmore
Mar 29, 2000·Journal of Pharmaceutical Sciences·D Pogocki, C Schöneich
Sep 22, 2010·The Journal of Physical Chemistry. B·Andrea L MillenStacey D Wetmore
Jun 27, 2007·Journal of the American Chemical Society·Yosuke Taniguchi, Eric T Kool

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