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Journal of Endotoxin Research
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IEIIS Meeting minireview: Chemical synthesis of peptidoglycan fragments for elucidation of the immunostimulating mechanism

Yukari Fujimoto

Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka, Japan

Seiichi Inamura

Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka, Japan

Akiko Kawasaki

Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka, Japan

Zenyu Shiokawa

Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka, Japan

Atsushi Shimoyama

Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka, Japan

Takashi Hashimoto

Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka, Japan

Shoichi Kusumoto

Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka, Japan, Suntory Institute for Bioorganic Research, Shimamoto-cho, Mishima-gun, Osaka, Japan

Koichi Fukase

Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka, Japan, koichi{at}chem.sci.osaka-u.ac.jp

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-{alpha} 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 {gamma}-D-glutamyl-meso-diaminopimelic acid (iE-DAP). Interaction of PGRPs with synthetic peptidoglycan fragments is also described.

Key Words: NOD1 • NOD2 • peptidoglycan • TLR2 • TLR4 • PGRP

Journal of Endotoxin Research, Vol. 13, No. 3, 189-196 (2007)
DOI: 10.1177/0968051907080739
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