51549-38-3Relevant academic research and scientific papers
Synthesis and properties of DNA oligomers containing 2′- deoxynucleoside N-oxide derivatives
Tsunoda, Hirosuke,Ohkubo, Akihiro,Taguchi, Haruhiko,Seio, Kohji,Sekine, Mitsuo
, p. 1217 - 1224 (2008)
(Chemical Equation Presented) Cytosine and adenine N-oxide derivatives have long been known as products resulting from the oxidative damage of DNA by peroxides such as hydrogen peroxide. Although the synthesis and properties of 2′-deoxynucleoside N-oxide
Exploring the synthesis of masked phosphoramido 6-vinylcytidine derivatives as building blocks for cross-linking oligonucleotides
Radi, Marco,Spinosa, Raffaella,Parlato, Maria Cristina,Corelli, Federico,Botta, Maurizio
, p. 151 - 166 (2008/02/09)
In the present work the synthesis of building blocks (2a,b), bearing a masked form of the reactive vinyl group bound to the C-6 position of a cytidine derivative, has been studied. The understanding of byproduct formation together with conformational considerations let us to plan a straightforward approach for the synthesis of the target compounds.
Structure-function studies on a synthetic guanosine receptor that simultaneously binds Watson-Crick and Hoogsteen sites
Quinn, Jordan R.,Zimmerman, Steven C.
, p. 7459 - 7467 (2007/10/03)
A series of receptors (11-16) designed to simultaneously bind the Watson-Crick and Hoogsteen sites of guanosine were synthesized, and their binding of guanosine tri-O-pentanoate (32) was probed via 1H NMR complexation studies in 5% DMSO-d6-chloroform-d. The guanosine receptors were synthesized with aminonaphthalene or aminoquinoline auxiliary groups tethered to N-4 of cytosine via a methylene or carbonyl group. A structure-function relationship was established allowing energetic contributions made by components of nucleoside analogues to be probed and more general design rules formulated that may guide the development of more efficacious DNA bases.
Unexpected shift to a 4-imino tautomer upon N4-acylation of 5- methylcytosin-1-yl nucleoside analogues
Busson,Kerremans,Van Aerschot,Peeters,Blaton,Herdewijn
, p. 1079 - 1082 (2007/10/03)
In contrast with the behaviour of 5-unsubstituted cytosine nucleoside analogues, 5-methylcytosine derivatives show upon N4-benzoylation, commonly used as base protection in oligonucleotide synthesis, a tautomeric change of the base moiety from a 4-amino- into a 4-imino isomer. In the latter form, which is easily diagnosticized by 13C NMR and confirmed by X-ray data, the compounds seem to be hydrolytically less stable.
