Synthesis of alpha-galactosyl ceramide, a potent immunostimulatory agent.
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.
Plettenburg
Oliver
O
Department of Chemistry and Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, California 92067, USA.
Bodmer-Narkevitch
Vera
V
Wong
Chi-Huey
CH
D000276:Adjuvants, Immunologic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D005690:Galactose / Q000031:analogs & derivatives / Q000737:chemistry; D005699:Galactosylceramides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006031:Glycosylation; D015394:Molecular Structure; D013237:Stereoisomerism
D000276:Adjuvants, Immunologic; D005699:Galactosylceramides; D005690:Galactose