Issue 30, 2013

Synthesis and biological activity of phosphoglycolipids from Thermus thermophilus

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-α). 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.

Graphical abstract: Synthesis and biological activity of phosphoglycolipids from Thermus thermophilus

Supplementary files

Article information

Article type
Paper
Submitted
30 Apr 2013
Accepted
29 Mei 2013
First published
26 Jun 2013

Org. Biomol. Chem., 2013,11, 5034-5041

Synthesis and biological activity of phosphoglycolipids from Thermus thermophilus

Y. Fujimoto, K. Mitsunobe, S. Fujiwara, M. Mori, M. Hashimoto, Y. Suda, S. Kusumoto and K. Fukase, Org. Biomol. Chem., 2013, 11, 5034 DOI: 10.1039/C3OB40899J

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