Synthesis of a Glycolipidic Amphiphilic Nitrone as a New Spin Trap.

J Org Chem

Laboratoire "Chimie Bioorganique et des Systèmes Moléculaires Vectoriels", Université d'Avignon et des Pays du Vaucluse, Faculté des Sciences, 33, rue Louis Pasteur, 84000-Avignon, France, and Laboratoire "Structure et Réactivité des Espèces Paramagnétiques", UMR 6517, CNRS et Universités d'Aix-Marseille I et III, Faculté de Saint Jérôme, case 521, 13397 Marseille Cedex 20, France.

Published: May 1999

The synthesis of a new amphiphilic nitrone, A, derived from a digalactosyl tris(hydroxymethyl)aminomethane bearing a perfluorocarbon chain is described. A exhibited a surfactant behavior (cmc = 1.6 x 10(-)(5) mol/L), and the specific recognition of the galactosyl moiety grafted on A by the KbCWL1 membrane lectin was established. Preliminary experiments showed that A was able to trap free radicals in aqueous media, the shape of the observed ESR spectra being strongly dependent upon the nature of the trapped free radical.

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http://dx.doi.org/10.1021/jo982343+DOI Listing

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