Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 14, Issue 33, Pages 10318-10330Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200801121
Keywords
carbohydrates; immunochemistry; peptides; tracheal cytotoxin
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Funding
- Scientific Research [17310128, 17510178, 19310144]
- Japan Society for the Promotion of Science
- Suntory Institute for Bioorgame Research
- NATIONAL INSTITUTE OF DENTAL & CRANIOFACIAL RESEARCH [R01DE018503] Funding Source: NIH RePORTER
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Bacterial cell wall peptidoglycan (PGN) is a potent immunostimulator and immune adjuvant. The PGN of Gram-negative bacteria and some Gram-positive bacteria contain meso-diaminopimelic acid (meso-DAP), and we have recently shown that the intracellular protein Nodl is a PGN receptor and recognizes DAP-containing peptides. In this study, we achieved the synthesis of DAP-containing PGN fragments, including the first chemical synthesis of tracheal NAC-L-Ala-gamma-D-Glu-meso-DAP-D-Ala, and a repeating-unit of DAP-type PGN, GlcNAc-(beta 1-4)-MurNAC-L-Ala-gamma-D-Glu-meso-DAP-D-Ala. For the synthesis of PGN fragments, we first established a new synthetic method for an orthogonally protected meso-DAP derivative, and then we constructed the glycopeptide structures. The ability of these fragments to stimulate human Nodl, as well as differences in Nodlrecognition of the variety of synthesized ligand structures were examined. The results showed that the substitution of the N terminus of iE-DAP is necessary for stronger Nodl recognition, but the structure of the substituent seems not to be strictly recognized. The importance of the carboxyl group at the 2-position of DAP for human Nod1 stimulation was also shown.
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