Structural features of 6-azacytidine and its derivatives: data of NMR and IR spectroscopies

Authors

  • S. P. Samijlenko Institute of Molecular Biology and Genetics, NAS of Ukraine 150, Akademika Zabolotnoho Str., Kyiv, Ukraine, 03680 Author
  • I. V. Alexeeva Institute of Molecular Biology and Genetics, NAS of Ukraine 150, Akademika Zabolotnoho Str., Kyiv, Ukraine, 03680 Author
  • L. H. Palchykivs'ka Institute of Molecular Biology and Genetics, NAS of Ukraine 150, Akademika Zabolotnoho Str., Kyiv, Ukraine, 03680 Author
  • I. V. Kondratyuk Institute of Molecular Biology and Genetics, NAS of Ukraine 150, Akademika Zabolotnoho Str., Kyiv, Ukraine, 03680 Author
  • A. V. Stepanyugin Institute of Molecular Biology and Genetics, NAS of Ukraine 150, Akademika Zabolotnoho Str., Kyiv, Ukraine, 03680 Author
  • A. S. Shalamay Institute of Molecular Biology and Genetics, NAS of Ukraine 150, Akademika Zabolotnoho Str., Kyiv, Ukraine, 03680 Author
  • D. M. Hovorun Institute of Molecular Biology and Genetics, NAS of Ukraine 150, Akademika Zabolotnoho Str., Kyiv, Ukraine, 03680 Author

DOI:

https://doi.org/10.7124/bc.0004A5

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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Published

1997-11-20

Issue

Vol. 13 No. 6 (1997)

Section

Structure and Function of Biopolymers