Synthesis of 5-N-tert-butylaminoxylcytidine and EPR studies on its base pairing properties

Mariko Aso, Yasuhiro Matsui, Bo Yang, Midori Sasagaki, Daiki Okado, Kazuteru Usui, Noboru Koga, Hiroshi Suemune

Research output: Contribution to journal › Article

2 Citations (Scopus)

Abstract

5-N-tert-Butylaminoxylcytidine was synthesized as a new spin-labelled cytidine to detect guanosine by EPR spectroscopy. Metal-halogen exchange reaction of TBS-protected N-benzoyl-5-iodocytidine followed by a reaction with 2-methyl-2-nitrosopropane afforded 5-N-tert-butylhydroxylaminocytidine with considerable affinity for guanosine and its oxidation gave 5-N-tert-butylaminoxylcytidine. Changes in EPR parameters monitored its selective base pairing with guanosine derivatives and the formation of a 2:2 complex with 8-oxoguanosine.

Original languageEnglish
Pages (from-to)5414-5419
Number of pages6
JournalTetrahedron
Volume71
Issue number33
DOIs
Publication statusPublished - Jul 11 2015

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Guanosine
Base Pairing
Paramagnetic resonance
Cytidine
Halogens
Spectrum Analysis
Metals
Spectroscopy
Derivatives
Oxidation

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Aso, M., Matsui, Y., Yang, B., Sasagaki, M., Okado, D., Usui, K., ... Suemune, H. (2015). Synthesis of 5-N-tert-butylaminoxylcytidine and EPR studies on its base pairing properties. Tetrahedron, 71(33), 5414-5419. https://doi.org/10.1016/j.tet.2015.05.080

Synthesis of 5-N-tert-butylaminoxylcytidine and EPR studies on its base pairing properties. / Aso, Mariko; Matsui, Yasuhiro; Yang, Bo; Sasagaki, Midori; Okado, Daiki; Usui, Kazuteru; Koga, Noboru; Suemune, Hiroshi.

In: Tetrahedron, Vol. 71, No. 33, 11.07.2015, p. 5414-5419.

Research output: Contribution to journal › Article

Aso, M, Matsui, Y, Yang, B, Sasagaki, M, Okado, D, Usui, K, Koga, N & Suemune, H 2015, 'Synthesis of 5-N-tert-butylaminoxylcytidine and EPR studies on its base pairing properties', Tetrahedron, vol. 71, no. 33, pp. 5414-5419. https://doi.org/10.1016/j.tet.2015.05.080
Aso M, Matsui Y, Yang B, Sasagaki M, Okado D, Usui K et al. Synthesis of 5-N-tert-butylaminoxylcytidine and EPR studies on its base pairing properties. Tetrahedron. 2015 Jul 11;71(33):5414-5419. https://doi.org/10.1016/j.tet.2015.05.080
Aso, Mariko ; Matsui, Yasuhiro ; Yang, Bo ; Sasagaki, Midori ; Okado, Daiki ; Usui, Kazuteru ; Koga, Noboru ; Suemune, Hiroshi. / Synthesis of 5-N-tert-butylaminoxylcytidine and EPR studies on its base pairing properties. In: Tetrahedron. 2015 ; Vol. 71, No. 33. pp. 5414-5419.
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