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 (JSmol)	Interactive image;
ChemSpider	9794910 ;
ECHA InfoCard	100.053.343
IUPHAR/BPS	5024;
MeSH	Muramyl+dipeptide
PubChem CID	11620162;
UNII	2U7S2HVO96 ;
CompTox Dashboard (EPA)	DTXSID90897421 ;
	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). verify (what is ?) Infobox references

Muramyl dipeptide is a component of bacterial peptidoglycan, a recognition structure or activator for nucleotide-binding oligomerization domain 2 (NOD2) protein.^[1] It is a 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, IL-1α and IL-1β especially.^[2]

Human NOD2 protein of the nucleotide-binding leucine-rich repeat family, is a cytoplasmic receptor involved in host innate immune system defense. Mutations in the CARD15 gene encoding NOD2 protein have been observed in Crohn's disease patients,^[3] decreasing the immune systems of these patients ability to recognize muramyl dipeptide. Analogues of muramyl dipeptide and their potential for immune response therapies in cancer and disease are being investigated.^[4] Experiments published in 2008 showed that muramyl dipeptide is involved in a molecular pathway in mice that conferred protection from colitis.^[5]

References

^ ^a ^b Inohara N, Ogura Y, Fontalba A, Gutierrez O, Pons F, Crespo J, et al. (February 2003). "Host recognition of bacterial muramyl dipeptide mediated through NOD2. Implications for Crohn's disease". The Journal of Biological Chemistry. 278 (8): 5509–5512. doi:10.1074/jbc.C200673200. hdl:10379/9336. PMID 12514169.
^ Martinon F, Agostini L, Meylan E, Tschopp J (November 2004). "Identification of bacterial muramyl dipeptide as activator of the NALP3/cryopyrin inflammasome". Current Biology. 14 (21): 1929–1934. doi:10.1016/j.cub.2004.10.027. PMID 15530394. S2CID 13728991.
^ Inohara N, Ogura Y, Fontalba A, Gutierrez O, Pons F, Crespo J, et al. (February 2003). "Host recognition of bacterial muramyl dipeptide mediated through NOD2. Implications for Crohn's disease". The Journal of Biological Chemistry. 278 (8): 5509–5512. doi:10.1074/jbc.c200673200. hdl:10379/9336. PMID 12514169.
^ Li X, Yu J, Xu S, Wang N, Yang H, Yan Z, et al. (July 2008). "Chemical conjugation of muramyl dipeptide and paclitaxel to explore the combination of immunotherapy and chemotherapy for cancer". Glycoconjugate Journal. 25 (5): 415–425. doi:10.1007/s10719-007-9095-3. PMID 18161023. S2CID 19058605.
^ Watanabe T, Asano N, Murray PJ, Ozato K, Tailor P, Fuss IJ, et al. (February 2008). "Muramyl dipeptide activation of nucleotide-binding oligomerization domain 2 protects mice from experimental colitis". The Journal of Clinical Investigation. 118 (2): 545–559. doi:10.1172/JCI33145. PMC 2176188. PMID 18188453.

[:0-1] Inohara N, Ogura Y, Fontalba A, Gutierrez O, Pons F, Crespo J, et al. (February 2003). "Host recognition of bacterial muramyl dipeptide mediated through NOD2. Implications for Crohn's disease". The Journal of Biological Chemistry. 278 (8): 5509–5512. doi:10.1074/jbc.C200673200. hdl:10379/9336. PMID 12514169.

[inflammasome2-2] Martinon F, Agostini L, Meylan E, Tschopp J (November 2004). "Identification of bacterial muramyl dipeptide as activator of the NALP3/cryopyrin inflammasome". Current Biology. 14 (21): 1929–1934. doi:10.1016/j.cub.2004.10.027. PMID 15530394. S2CID 13728991.

[3] Inohara N, Ogura Y, Fontalba A, Gutierrez O, Pons F, Crespo J, et al. (February 2003). "Host recognition of bacterial muramyl dipeptide mediated through NOD2. Implications for Crohn's disease". The Journal of Biological Chemistry. 278 (8): 5509–5512. doi:10.1074/jbc.c200673200. hdl:10379/9336. PMID 12514169.

[Li_2008-4] Li X, Yu J, Xu S, Wang N, Yang H, Yan Z, et al. (July 2008). "Chemical conjugation of muramyl dipeptide and paclitaxel to explore the combination of immunotherapy and chemotherapy for cancer". Glycoconjugate Journal. 25 (5): 415–425. doi:10.1007/s10719-007-9095-3. PMID 18161023. S2CID 19058605.

[5] Watanabe T, Asano N, Murray PJ, Ozato K, Tailor P, Fuss IJ, et al. (February 2008). "Muramyl dipeptide activation of nucleotide-binding oligomerization domain 2 protects mice from experimental colitis". The Journal of Clinical Investigation. 118 (2): 545–559. doi:10.1172/JCI33145. PMC 2176188. PMID 18188453.

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See also

References