Synthesis and evaluation of stimulatory properties of Sphingomonadaceae glycolipids.
Glycosphingolipids (GSLs) from the Sphingomonadaceae family of bacteria have been reported to be potent stimulators of natural killer T cells. These glycolipids include mono-, tri- and tetraglycosylceramides. Here we have prepared the GSL-1 to GSL-4 series of glycolipids and tested their abilities to stimulate natural killer T cells. Among these glycolipids, only GSL-1 (1) is a potent stimulator. Using a series of synthetic diglycosylceramides, we show that oligoglycosylceramides from Sphingomonadaceae are not effectively truncated to GSL-1 in lysosomes in antigen-presenting cells, possibly because the higher-order GSLs are poor substrates for lysosomal acyltransfer enzymes.
Department of Chemistry and Biochemistry, C100 BNSN, Brigham Young University, Provo, Utah 84602, USA.
Xiangtian
X
Long
Shenglou
S
Deng
Jochen
J
Mattner
Zhuo
Z
Zang
Dapeng
D
Zhou
Nathan
N
McNary
Randal D
RD
Goff
Luc
L
Teyton
Albert
A
Bendelac
Paul B
PB
Savage
D017951:Antigen Presentation; D000938:Antigen-Presenting Cells / Q000187:drug effects / Q000276:immunology; D006017:Glycolipids / Q000138:chemical synthesis* / Q000276:immunology* / Q000378:metabolism; D006028:Glycosphingolipids / Q000276:immunology*; D006801:Humans; D007694:Killer Cells, Natural / Q000276:immunology; D008247:Lysosomes / Q000378:metabolism; D042301:Sphingomonadaceae / Q000737:chemistry*
D006017:Glycolipids; D006028:Glycosphingolipids; C119144:glycosphingolipid GSL-1