Synthesis and biological activity of alpha-galactosyl ceramide KRN7000 and galactosyl (alpha1-->2) galactosyl ceramide.
We herein report a faster and less cumbersome synthesis of the biologically attractive, alpha-galactosyl ceramide (alpha-GalCer), known as KRN7000, and its analogues. More importantly, the use of a silicon tethered intramolecular glycosylation reaction gave easy access to the diglycosyl ceramide Gal(alpha1-->2)GalCer, which has been shown to require uptake and processing to the biologically active alpha-GalCer derivative.
Veerapen
Natacha
N
School of Biosciences, University of Birmingham, Edgbaston, Birmingham B15 2TT, UK.
Brigl
Manfred
M
Garg
Salil
S
Cerundolo
Vincenzo
V
Cox
Liam R
LR
Brenner
Michael B
MB
Besra
Gurdyal S
GS
D000818:Animals; D055610:Antigens, CD1d / Q000737:chemistry; D000970:Antineoplastic Agents / Q000737:chemistry* / Q000494:pharmacology; D045744:Cell Line, Tumor; D002626:Chemistry, Pharmaceutical / Q000379:methods; D015195:Drug Design; D005699:Galactosylceramides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006027:Glycosides / Q000737:chemistry; D006801:Humans; D007694:Killer Cells, Natural / Q000166:cytology; D051379:Mice; D008956:Models, Chemical; D018418:Th2 Cells / Q000378:metabolism
D055610:Antigens, CD1d; D000970:Antineoplastic Agents; D005699:Galactosylceramides; D006027:Glycosides; C493154:alpha-galactosylceramide; C103873:KRN 7000