Synthesis of peptidoglycan fragments and evaluation of their biological activity

Seiichi Inamura, Yukari Fujimoto, Akiko Kawasaki, Zenyu Shiokawa, Eva Woelk, Holger Heine, Buko Lindner, Naohiro Inohara, Shoichi Kusumoto, Koichi Fukase

研究成果: Article査読

61 被引用数 (Scopus)

抄録

The peptidoglycan (PG) bacterial cell wall glycoconjugate has been well known as a strong immunopotentiator. Partial structures of PG were chemically synthesized for elucidation of precise biological activities. Effective construction of distinct repeating glycans of PG was accomplished by the coupling of a key disaccharide glucosaminyl-β(1-4)-muramic acid unit. Stereoselective glycosylation of disaccharide units was achieved by neighboring group participation of the N-Troc (Troc = 2,2,2-trichloroethoxycarbonyl) group and appropriate reactivity of N-Troc-glucosaminyl trichloroacetimidate. By using an efficient synthetic strategy, mono-, di-, tetra- and octasaccharide fragments of PG were synthesized in high yields. The biological activity of synthetic fragments of PG was evaluated by induction of tumor necrosis factor-α (TNF-α) from human monocytes, and toll-like receptor 2 (TLR2) and Nod2 dependencies by using transfected HEK293 cells, respectively. Here we reveal that TLR2 was not stimulated by the series of synthetic PG partial structures, whereas Nod2 recognizes the partial structures containing the MDP moiety.

本文言語English
ページ(範囲)232-242
ページ数11
ジャーナルOrganic and Biomolecular Chemistry
4
2
DOI
出版ステータスPublished - 2006 4 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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