Synthesis and Evaluation of NAcetyl2amino2deoxyαDgalactosyl 1Thio7oxaceramide, a New Analogue of αDGalactosyl Ceramide.

Autor: Roshini Rajan, Thresen Mathew, Radovan Buffa, Frédéric Bornancin, Marco Cavallari, Peter Nussbaumer, Gennaro DeLibero, Andrea Vasella
Zdroj: Helvetica Chimica Acta; May2009, Vol. 92 Issue 5, p918-927, 10p
Abstrakt: The Nacetyl2amino2deoxyαDgalactopyranosyl 1thio7oxaceramide 1was synthesized by substituting the 7oxasphingosine triflate 3with αDNacetyl1thiogalactosamine 2. The triflate 3was obtained from azide 4. Thiol 2was prepared according to a known procedure from αDgalactosamine hydrochloride. As compared to ceramide Cer, 1is neither a substrate of ceramide kinase CerK, consistent with the absence of the C1OH group, nor an inhibitor of Cer phosphorylation by CerK. While 1partially displaced CD1dbound lipids, it failed to stimulate invariant natural killer T iNKT cells when presented by human CD1dtransfected cells. These results suggest that 1binds weakly to recombinant CD1d, but does not form immunogenic complexes with CD1d. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index