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 journalArticlepeer-review

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

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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