Synthesis of alpha-galactosyl ceramide,a potent immunostimulatory agent |
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Authors: | Plettenburg Oliver Bodmer-Narkevitch Vera Wong Chi-Huey |
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Institution: | Department of Chemistry and Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, California 92067, USA. |
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Abstract: | Alpha-galactosyl ceramide has been identified to be a potent stimulatory agent for a novel immunological process, mediated by CD1 molecules. This paper describes a short and efficient synthesis of alpha-galactosyl ceramide. Starting from commercially available 2-deoxy galactose, a suitable sphingosine derivative was obtained in nine steps and 36% overall yield, which was subsequently glycosylated to give the target molecule. This flexible route will provide various glycolipids for further exploration of this interesting biological process. |
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