total synthesis of 1-2-docosanoylamino-O-(2-O-methyl-α -D-galactopyranosyl)-1,3,4-octadecanetriol (2), a 2′-methoxy analog of the immunostimulating α-galactoglycosphingolipid 1, is reported. Stereoselective α-glycosylation of the azido precursor of sphingosine was successfully performed for the first time using an improved Mukaiyama reaction. When assayed in a 72 h splenocyte proliferation test, compound 2 was significantly less stimulatory than the non-methylated compound 1, suggesting that the galactose 2-OH group is essential for the immunostimulatory activity of α-Gal-GSLs.
Immunomodulatory a-galactosyl glycosphingolipids : synthesis of a 2'-O-methyl- a -galactosyl-GSL and evaluation of its immunostimulating capacity / L. Barbieri, V. Costantino, E. Fattorusso, A. Mangoni, E. Aru, S. Parapini, D. Taramelli. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2004:3(2004 Feb), pp. 468-473. [10.1002/ejoc.200300512]
Immunomodulatory a-galactosyl glycosphingolipids : synthesis of a 2'-O-methyl- a -galactosyl-GSL and evaluation of its immunostimulating capacity
S. ParapiniPenultimo
;D. TaramelliUltimo
2004
Abstract
total synthesis of 1-2-docosanoylamino-O-(2-O-methyl-α -D-galactopyranosyl)-1,3,4-octadecanetriol (2), a 2′-methoxy analog of the immunostimulating α-galactoglycosphingolipid 1, is reported. Stereoselective α-glycosylation of the azido precursor of sphingosine was successfully performed for the first time using an improved Mukaiyama reaction. When assayed in a 72 h splenocyte proliferation test, compound 2 was significantly less stimulatory than the non-methylated compound 1, suggesting that the galactose 2-OH group is essential for the immunostimulatory activity of α-Gal-GSLs.Pubblicazioni consigliate
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