866030-91-3Relevant academic research and scientific papers
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 (2005)
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.
Synthesis of 2-fluoro and 4-fluoro galactopyranosyl phosphonate analogues of UDP-Gal
Jambal, Irekhjargal,Kefurt, Karel,Hlavackova, Martina,Moravcova, Jitka
, p. 31 - 39,9 (2020/07/30)
Two novel nonisosteric UDP-Gal analogues, (2-deoxy-2-fluoro- and 4-deoxy-4-fluoro-α-D-galactopyranosyl) phosphonoyl phosphates, were synthesized by optimized multistep procedures starting from 3,4,6-tri-O-benzyl- D-galactal and allyl 2,3,6-tri-O-benzyl-α-D-glucopyranoside, respectively. The key steps were a Michaelis-Arbuzov reaction of respective deoxy-fluoro-D-galactopyranosyl acetate with triethyl phosphite followed by a Moffatt-Khorana coupling reaction with UMP-morpholidate. The structure of all new compounds was confirmed by NMR and mass spectroscopies.
