866030-97-9Relevant articles and documents
Immunomodulatory α-galactoglycosphingolipids: Synthesis of 2′-fluoro-2′-deoxy-α-galactosylceramide and an evaluation of its immunostimulating properties
Barbieri, Lucia,Costantino, Valeria,Fattorusso, Ernesto,Mangoni, Alfonso,Basilico, Nicoletta,Mondani, Monica,Taramelli, Donatella
, p. 3279 - 3285 (2007/10/03)
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. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.