Muramyl dipeptide
 | |
| Names | |
|---|---|
| IUPAC name
(4R)-4-[ [(2S)-2-[ [(2R)-2-[(2R,5S)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxypropanoyl]amino]propanoyl]amino]-5-amino-5-oxopentanoic acid | |
| Other names
Acetylmuramyl-Alanyl-Isoglutamine | |
| Identifiers | |
53678-77-6  | |
| ChemSpider | 9794910 |
| 5024 | |
| Jmol interactive 3D | Image |
| MeSH | Muramyl+dipeptide |
| PubChem | 11620162 |
| |
| |
| Properties | |
| C19H32N4O11 | |
| Molar mass | 492.47758 |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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| Infobox references | |
Muramyl dipeptide is constituent of both Gram-positive and Gram-negative bacteria composed of N-acetylmuramic acid linked by its lactic acid moiety to the N-terminus of an L-alanine D-isoglutamine dipeptide.[1]
It can be recognized by the immune system as a pathogen-associated molecular pattern and activate the NALP3 inflammasome which in turn leads to cytokine activation, especially IL-1α and IL-1β. [2]
See also
- Dipeptide
- Mifamurtide, a synthetic analogue for the treatment of osteosarcoma
References
- ↑ Inohara, N.; Ogura, Y.; Fontalba, A.; Gutierrez, O.; Pons, F.; Crespo, J.; Fukase, K.; Inamura, S.; Kusumoto, S.; Hashimoto, M.; Foster, S. J.; Moran, A. P.; Fernandez-Luna, J. L.; Nuñez, G. (2003). "Host Recognition of Bacterial Muramyl Dipeptide Mediated through NOD2. Implications for Crohn's Disease". Journal of Biological Chemistry 278 (8): 5509–5512. doi:10.1074/jbc.C200673200. PMID 12514169.
- ↑ Curr Biol. 2004 Nov 9;14(21):1929-34., Martinon F, Agostini L, Meylan E, Tschopp J. Identification of bacterial muramyl dipeptide as activator of the NALP3/cryopyrin inflammasome..
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