Spin labeled nucleoside analogues: 4‘-hydroxymorpholin-2’-ylpurines and pyrimidines

Jean M.J. Tronchet, M. Martina Zsely, D. Daniel Cabrini, C. Chantal Jorand, F. Frangoise Barbalat-Rey, I. Istvan Komaromi, A. Alessandra Ricca, M. Michel Geoffroy

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Upon borane-pyridine reduction, a series of nucleoside dialdehyde dioximes 2 underwent cyclization to the corresponding 4’-hydroxymorpholin-2’-ylpurines or pyrimidines 3 from which the peracetyl derivatives 4 were prepared. At room temperature, compounds 3 and 4 exist as a mixture of invertomers in which the 4’S (equatorial 4’-OH or 4’-OAc) predominates. A 14 kcal/mol, nitrogen inversion barrier was estimated from variable temperature experiments. N.O.E. and 3JCHmeasurements established the anti conformation of the base-”sugar” bond. Compounds 3 spontaneously oxidized to the corresponding aminoxyl free radicals, EPR spectra of which showed that they existed in a chair conformation.

Original languageEnglish
Pages (from-to)615-629
Number of pages15
JournalNucleosides and Nucleotides
Volume12
Issue number6
DOIs
Publication statusPublished - Jul 1 1993

ASJC Scopus subject areas

  • Biochemistry
  • Genetics

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    Tronchet, J. M. J., Martina Zsely, M., Daniel Cabrini, D., Chantal Jorand, C., Frangoise Barbalat-Rey, F., Istvan Komaromi, I., Alessandra Ricca, A., & Michel Geoffroy, M. (1993). Spin labeled nucleoside analogues: 4‘-hydroxymorpholin-2’-ylpurines and pyrimidines. Nucleosides and Nucleotides, 12(6), 615-629. https://doi.org/10.1080/07328319308019016