In the framework of a project to assess the immunomodulating properties of α-galactosyl glycosphingolipids, the total synthesis of 1-O-(2-fluoro-2-deoxy-α-D-galactopyranosyl)-2-docosanoylamino-1,3, 4-octadecanetriol (1), a 2′-fluoro analogue of the immunostimulating α-galactoglycosphingolipids, was accomplished. The glycosidation reaction of the azido precursor of sphingosine was performed using the Mukaiyama glycosidation reaction. The stimulation of mouse splenocyte proliferation by the 2′-fluoro analogue was highly reduced compared to that of the α-galactoglycosphingolipids, thereby confirming that a free galactose 2-OH group is essential for the immunostimulatory activity.

Immunomodulatory-Galactoglycosphingolipids : Synthesis of 2'-Fluoro-2'-deoxy--galactosylceramide and an Evaluation of Its Immunostimulating Properties / L. Barbieri, V. Costantino, E. Fattorusso, A. Mangoni, N. Basilico, M. Mondani, D. Taramelli. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2005:15(2005 Aug), pp. 3279-3285. [10.1002/ejoc.200500053]

Immunomodulatory-Galactoglycosphingolipids : Synthesis of 2'-Fluoro-2'-deoxy--galactosylceramide and an Evaluation of Its Immunostimulating Properties

N. Basilico;M. Mondani
Penultimo
;
D. Taramelli
Ultimo
2005

Abstract

In the framework of a project to assess the immunomodulating properties of α-galactosyl glycosphingolipids, the total synthesis of 1-O-(2-fluoro-2-deoxy-α-D-galactopyranosyl)-2-docosanoylamino-1,3, 4-octadecanetriol (1), a 2′-fluoro analogue of the immunostimulating α-galactoglycosphingolipids, was accomplished. The glycosidation reaction of the azido precursor of sphingosine was performed using the Mukaiyama glycosidation reaction. The stimulation of mouse splenocyte proliferation by the 2′-fluoro analogue was highly reduced compared to that of the α-galactoglycosphingolipids, thereby confirming that a free galactose 2-OH group is essential for the immunostimulatory activity.
Settore MED/04 - Patologia Generale
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/18010
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