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

Research output: Contribution to journalArticle

7 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)5034-5041
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume11
Issue number30
DOIs
Publication statusPublished - 2013 Aug 14
Externally publishedYes

Fingerprint

Thermus thermophilus
glycerols
activity (biology)
Bioactivity
Glycerol
synthesis
thermophiles
configurations
Glycosylation
glucosides
Stereochemistry
Glycolipids
stereochemistry
Glycosides
Immunization
Interleukin-6
induction
analogs
Cytokines
proteins

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Biochemistry

Cite this

Fujimoto, Y., Mitsunobe, K., Fujiwara, S., Mori, M., Hashimoto, M., Suda, Y., ... Fukase, K. (2013). Synthesis and biological activity of phosphoglycolipids from Thermus thermophilus. Organic and Biomolecular Chemistry, 11(30), 5034-5041. https://doi.org/10.1039/c3ob40899j

Synthesis and biological activity of phosphoglycolipids from Thermus thermophilus. / Fujimoto, Yukari; Mitsunobe, Kunihiro; Fujiwara, Satoko; Mori, Motoko; Hashimoto, Masahiro; Suda, Yasuo; Kusumoto, Shoichi; Fukase, Koichi.

In: Organic and Biomolecular Chemistry, Vol. 11, No. 30, 14.08.2013, p. 5034-5041.

Research output: Contribution to journalArticle

Fujimoto, Y, Mitsunobe, K, Fujiwara, S, Mori, M, Hashimoto, M, Suda, Y, Kusumoto, S & Fukase, K 2013, 'Synthesis and biological activity of phosphoglycolipids from Thermus thermophilus', Organic and Biomolecular Chemistry, vol. 11, no. 30, pp. 5034-5041. https://doi.org/10.1039/c3ob40899j
Fujimoto, Yukari ; Mitsunobe, Kunihiro ; Fujiwara, Satoko ; Mori, Motoko ; Hashimoto, Masahiro ; Suda, Yasuo ; Kusumoto, Shoichi ; Fukase, Koichi. / Synthesis and biological activity of phosphoglycolipids from Thermus thermophilus. In: Organic and Biomolecular Chemistry. 2013 ; Vol. 11, No. 30. pp. 5034-5041.
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