Biopolym. Cell. 1997; 13(6):445-452.
http://dx.doi.org/10.7124/bc.0004A5
Structure and Function of Biopolymers
Structural features of 6-azacytidine and its derivatives: data of NMR and IR spectroscopies
1Samijlenko S. P., 1Alexeeva I. V., 1Palchykivs'ka L. H., 1Kondratyuk I. V., 1Stepanyugin A. V., 1Shalamay A. S., 1Hovorun D. M.
  1. Institute of Molecular Biology and Genetics, NAS of Ukraine
    150, Akademika Zabolotnoho Str., Kyiv, Ukraine, 03680

Abstract

Study of 6-azaCyt, 6-azaC, a number of their derivatives and related compounds was conducted by IR and NMR spectrocsopies. Doublet splitting of amino group signal in NMR spectra of 6-azaCyt (unlike the cases of canonical base Cyt, nucleosides C and dC under the same experimental conditions) indicates nonequivalency of amino protons caused by greater asymmetry of electron structure which increases on ring substitutions at the 1 and 5 positions and increased barrier of amino group rotation. The dow field component of the doublet is only responsive to the 5-methyl substitution, as probably related to the involvement one of amino protons into an intramolecular H-bond with the N3 atom. Inverse (as compared to Cyt) specificity of interactions of 6-zaCyt with the amino acid carboxylic group and carboxylate-ion in anhydrous DMSO has been shown. The spectroscopy data support the conclusion that investigated compounds with nonsubstituted amino group exist as keto-amino tautomers in DMSO and solid state.
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