Muramyl dipeptide

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
CAS Number	53678-77-6
3D model (Jmol)	Interactive image
ChemSpider	9794910
ECHA InfoCard	100.053.343
IUPHAR/BPS	5024
MeSH	Muramyl+dipeptide
PubChem	11620162
InChI InChI=1S/C19H32N4O11/c1-7(17(30)23-10(16(20)29)4-5-12(26)27)21-18(31)8(2)33-15-13(22-9(3)25)19(32)34-11(6-24)14(15)28/h7-8,10-11,13-15,19,24,28,32H,4-6H2,1-3H3,(H2,20,29)(H,21,31)(H,22,25)(H,23,30)(H,26,27)/t7-,8+,10+,11+,13+,14+,15+,19?/m0/s1 Key: BSOQXXWZTUDTEL-QAQREVAFSA-N InChI=1/C19H32N4O11/c1-7(17(30)23-10(16(20)29)4-5-12(26)27)21-18(31)8(2)33-15-13(22-9(3)25)19(32)34-11(6-24)14(15)28/h7-8,10-11,13-15,19,24,28,32H,4-6H2,1-3H3,(H2,20,29)(H,21,31)(H,22,25)(H,23,30)(H,26,27)/t7-,8+,10+,11+,13+,14+,15+,19?/m0/s1 Key: BSOQXXWZTUDTEL-QAQREVAFBN
SMILES O=C(N)[C@H](NC(=O)[C@@H](NC(=O)[C@H](O[C@H]1[C@H](O)[C@H](OC(O)[C@@H]1NC(=O)C)CO)C)C)CCC(=O)O
Properties
Chemical formula	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

1. 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.
2. 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..