Letter abstract
Nature Chemical Biology 3, 559 - 564 (2007)
Published online: 29 July 2007 | doi:10.1038/nchembio.2007.19
Synthesis and evaluation of stimulatory properties of Sphingomonadaceae glycolipids
Xiangtian Long1,5, Shenglou Deng1,5, Jochen Mattner2, Zhuo Zang1, Dapeng Zhou3, Nathan McNary1, Randal D Goff1, Luc Teyton4, Albert Bendelac2 & Paul B Savage1
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.
- Department of Pathology, 57 East 7th Street, University of Chicago, Chicago, Illinois 60637, USA.
- Department of Melanoma Medical Oncology, University of Texas M.D. Anderson Cancer Center, 7455 Fannin Street, Houston, Texas 77054, USA.
- Immunology Department, 10550 North Torrey Pines Road, Scripps Research Institute, La Jolla, California 92037, USA.
- These authors contributed equally to this work.
Correspondence to: Paul B Savage1 e-mail: paul_savage@byu.edu
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