Spin labelled C-glycoside analogs: Derivatives of 1, 4-anhydro-4-deoxy-2, 3-O-cyclopentylidene-l, 4-N- hydroxyimino-dl-erythrofuranose

Jean M.J. Tronchet, Mirna Balkadhjian, Guido Zosimo-Landolfo, Françoise Barbalat-Rey, Patrick Lichtle, Alessandra Ricca, Istvan Komaromi

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Abstract

A series of 2, 3-O-cyclopentylidene C-glycoside analogs in which the furanose ring has been replaced with a N-hydroxypyrrolidine have been prepared. A structural study of these tricyclic compounds and the aminoxyl radicals thereof has been carried out using variable temperature 1H NMR, X-ray diffraction, molecular dynamics and EPR spectroscopy. Both types of compounds, N-hydroxypyrrolidines and pyrrolidine N-oxyls, fundamentally prefer - in solutions - N-endo conformations over the alternate, N-exo forms found by X-ray diffraction studies and computed to be more stable by molecular dynamics.

Original languageEnglish
Pages (from-to)17-34
Number of pages18
JournalJournal of Carbohydrate Chemistry
Volume14
Issue number1
DOIs
Publication statusPublished - Jan 1 1995

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ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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