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Nat Chem Biol. 2007 Sep;3(9):559-64. Epub 2007 Jul 29.

Synthesis and evaluation of stimulatory properties of Sphingomonadaceae glycolipids.

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Department of Chemistry and Biochemistry, C100 BNSN, Brigham Young University, Provo, Utah 84602, USA.


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.

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