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, I. Komáromi

Research output: Contribution to journalArticle

5 Citations (Scopus)

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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Molecular Dynamics Simulation
X-Ray Diffraction
Molecular dynamics
Derivatives
X ray diffraction
Paramagnetic resonance
Conformations
Spectrum Analysis
Nuclear magnetic resonance
Spectroscopy
Temperature
C-glycoside
endo-alpha-sialidase
pyrrolidine
Proton Magnetic Resonance Spectroscopy

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

Cite this

Spin labelled C-glycoside analogs : Derivatives of 1, 4-anhydro-4-deoxy-2, 3-O-cyclopentylidene-l, 4-N- hydroxyimino-dl-erythrofuranose. / Tronchet, Jean M J; Balkadhjian, Mirna; Zosimo-Landolfo, Guido; Barbalat-Rey, Françoise; Lichtle, Patrick; Ricca, Alessandra; Komáromi, I.

In: Journal of Carbohydrate Chemistry, Vol. 14, No. 1, 01.01.1995, p. 17-34.

Research output: Contribution to journalArticle

Tronchet, Jean M J ; Balkadhjian, Mirna ; Zosimo-Landolfo, Guido ; Barbalat-Rey, Françoise ; Lichtle, Patrick ; Ricca, Alessandra ; Komáromi, I. / Spin labelled C-glycoside analogs : Derivatives of 1, 4-anhydro-4-deoxy-2, 3-O-cyclopentylidene-l, 4-N- hydroxyimino-dl-erythrofuranose. In: Journal of Carbohydrate Chemistry. 1995 ; Vol. 14, No. 1. pp. 17-34.
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