Immunomodulatory α-Galactoglycosphingolipids: Synthesis of a 2′-O-Methyl-α-Gal-GSL and Evaluation of Its Immunostimulating Capacity

The 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 f...

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Bibliographic Details
Published in:European journal of organic chemistry 2004-02, Vol.2004 (3), p.468-473
Main Authors: Barbieri, Lucia, Costantino, Valeria, Fattorusso, Ernesto, Mangoni, Alfonso, Aru, Elisabetta, Parapini, Silvia, Taramelli, Donatella
Format: Article
Language:English
Subjects:
Glycolipids
Glycosylation
Immunomodulatory activity
Sphingolipids
Total synthesis
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Summary:The 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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200300512