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.
Long
Xiangtian
X
Department of Chemistry and Biochemistry, C100 BNSN, Brigham Young University, Provo, Utah 84602, USA.
Deng
Shenglou
S
Mattner
Jochen
J
Zang
Zhuo
Z
Zhou
Dapeng
D
McNary
Nathan
N
Goff
Randal D
RD
Teyton
Luc
L
Bendelac
Albert
A
Savage
Paul B
PB
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