Journal
CARBOHYDRATE RESEARCH
Volume 341, Issue 17, Pages 2785-2798Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2006.09.006
Keywords
alpha-galactosyl-ceramide; iNKT cells; lipid antigen presentation; CD1d; agelasphins; KRN 7000
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alpha-Galactosyl-ceramide (1) has been identified as a powerful modulator of immunological processes through its capacity to bind CD1d molecules and specifically activate invariant natural killer (NK)-like T cells (iNKT cells). This paper describes the synthesis of 1, the analogous alpha-galactosyl-ceramide 3, and its short chain analogue 'OCH' (2), by use of the 4,6-di-O-tert-butylsilylene (DTBS) protecting group to produce a powerful alpha-galactosylating agent. In vivo experiments confirmed these compounds to be potent and selective activators of iNKT cells in a CD1d-dependent manner, each inducing a unique profile of cytokine release. This synthesis strategy will permit the generation of novel derivatives for use in the study of the mechanism of iNKT cell activation. (c) 2006 Elsevier Ltd. All rights reserved.
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