Chemical synthesis of peptidoglycan fragments for elucidation of the immunostimulating mechanism

Yukari Fujimoto, Seiichi Inamura, Akiko Kawasaki, Zenyu Shiokawa, Atsushi Shimoyama, Takashi Hashimoto, Shoichi Kusumoto, Koichi Fukase

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Partial structures of peptidoglycan were chemically synthesized for elucidation of their precise biological activities. By using an efficient synthetic strategy, mono-, di-, tetra- and octasaccharide fragments of peptidoglycan were synthesized in good yields. The biological activity of synthetic fragments of peptidoglycan was evaluated by induction of TNF-α from human monocytes, and TLR2 and NOD2 dependencies by using transfected HEK293 cells, respectively. We revealed that TLR2 was not stimulated by the series of synthetic peptidoglycan partial structures, whereas NOD2 recognizes the partial structures containing the MDP moiety. We also synthesized potent NOD1 agonists, which showed several hundred-fold stronger activity than γ-D-glutamyl-meso-diaminopimelic acid (iE-DAP). Interaction of PGRPs with synthetic peptidoglycan fragments is also described.

Original languageEnglish
Pages (from-to)189-196
Number of pages8
JournalJournal of Endotoxin Research
Volume13
Issue number3
DOIs
Publication statusPublished - 2007 Jun
Externally publishedYes

Fingerprint

Peptidoglycan
Bioactivity
Diaminopimelic Acid
HEK293 Cells
Monocytes

Keywords

  • NOD1
  • NOD2
  • Peptidoglycan
  • PGRP
  • TLR2
  • TLR4

ASJC Scopus subject areas

  • Microbiology
  • Immunology
  • Toxicology

Cite this

Chemical synthesis of peptidoglycan fragments for elucidation of the immunostimulating mechanism. / Fujimoto, Yukari; Inamura, Seiichi; Kawasaki, Akiko; Shiokawa, Zenyu; Shimoyama, Atsushi; Hashimoto, Takashi; Kusumoto, Shoichi; Fukase, Koichi.

In: Journal of Endotoxin Research, Vol. 13, No. 3, 06.2007, p. 189-196.

Research output: Contribution to journalArticle

Fujimoto, Y, Inamura, S, Kawasaki, A, Shiokawa, Z, Shimoyama, A, Hashimoto, T, Kusumoto, S & Fukase, K 2007, 'Chemical synthesis of peptidoglycan fragments for elucidation of the immunostimulating mechanism', Journal of Endotoxin Research, vol. 13, no. 3, pp. 189-196. https://doi.org/10.1177/0968051907080739
Fujimoto, Yukari ; Inamura, Seiichi ; Kawasaki, Akiko ; Shiokawa, Zenyu ; Shimoyama, Atsushi ; Hashimoto, Takashi ; Kusumoto, Shoichi ; Fukase, Koichi. / Chemical synthesis of peptidoglycan fragments for elucidation of the immunostimulating mechanism. In: Journal of Endotoxin Research. 2007 ; Vol. 13, No. 3. pp. 189-196.
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