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

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Abstract

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.

Original languageEnglish
Pages (from-to)232-242
Number of pages11
JournalOrganic and Biomolecular Chemistry
Volume4
Issue number2
DOIs
Publication statusPublished - 2006 Apr 14

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ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Inamura, S., Fujimoto, Y., Kawasaki, A., Shiokawa, Z., Woelk, E., Heine, H., Lindner, B., Inohara, N., Kusumoto, S., & Fukase, K. (2006). Synthesis of peptidoglycan fragments and evaluation of their biological activity. Organic and Biomolecular Chemistry, 4(2), 232-242. https://doi.org/10.1039/b511866b