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. Parapini
Penultimo
;
D. Taramelli
Ultimo
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.
Glycolipids; Glycosylation; Immunomodulatory activity; Sphingolipids; Total synthesis
Settore MED/04 - Patologia Generale
feb-2004
Article (author)
File in questo prodotto:
Non ci sono file associati a questo prodotto.
Pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/18356
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 32
  • ???jsp.display-item.citation.isi??? 33
social impact