Synthesis and biological activity of phosphoglycolipids from Thermus thermophilus

Yukari Fujimoto, Kunihiro Mitsunobe, Satoko Fujiwara, Motoko Mori, Masahiro Hashimoto, Yasuo Suda, Shoichi Kusumoto, Koichi Fukase

研究成果: Article査読

12 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)5034-5041
ページ数8
ジャーナルOrganic and Biomolecular Chemistry
11
30
DOI
出版ステータスPublished - 2013 8月 14
外部発表はい

ASJC Scopus subject areas

  • 生化学
  • 物理化学および理論化学
  • 有機化学

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