期刊
ORGANIC & BIOMOLECULAR CHEMISTRY
卷 11, 期 30, 页码 5034-5041出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c3ob40899j
关键词
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资金
- Japan Society for the Promotion of Science
- Suntory Institute for Bioorganic Research (SUNBOR Grant)
- Houansha Foundation
- Takeda Science Foundation
- Naito Foundation
- Osaka University Global COE program (Frontier Biomedical Science Underlying Organelle Network Biology)
- ERATO
- Murata Lipid Active Structure Project
- JSPS [LR025]
- CSTP [LR025]
- Grants-in-Aid for Scientific Research [23300356] Funding Source: KAKEN
An extreme thermophile, Thermus thermophilus, has very unique glycolipids on the cell surface. The acidic immunostimulatory phosphoglycolipid of T thermophilus was synthesized for the first time, with newly developed glycosylation methods using 3-nitropyridyl (3NPy) and 4,6-dimethoxy-1,3,5-triazin-2-yl (DMT) glycosides as glycosyl donors. The analogues of the phosphoglycolipid, which include a diastereomer possessing the opposite configuration at the diacyl glycerol moiety, were also synthesized. The biological activities of the synthesized compounds were elucidated with cytokine inductions (IL-6 and TNF-alpha). A synthetic phosphoglycolipid with a natural-type diacyl glycerol configuration showed apparent immunostimulatory activity, whereas its diastereomer did not. The present study revealed that the configuration at the diacyl glycerol moiety of the phosphoglycolipids is important for immunostimulation, suggesting the existence of the particular receptor/recognizing protein that can recognize the stereochemistry of the glycerol part.
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