☆ 4.6 Article

Synthesis and biological activity of phosphoglycolipids from Thermus thermophilus

ORGANIC & BIOMOLECULAR CHEMISTRY (2013)

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY

Volume 11, Issue 30, Pages 5034-5041

Publisher

ROYAL SOC CHEMISTRY

DOI: 10.1039/c3ob40899j

Keywords

-

Categories

Chemistry, Organic

Funding

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

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Abstract

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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