Muramyl dipeptide: Difference between revisions

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
MeSH	Muramyl+dipeptide
PubChem CID	11620162;
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

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Muramyl dipeptide is a peptidoglycan constituent of both Gram positive and Gram negative bacteria. It is 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 PAMP (pathogen associated molecular pattern)and activate the NALP3 inflammasome which in turn leads to cytokine activation, especially IL-1α and IL-1β. ^[2]

References

^ 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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[1] PMID 12514169

[inflammasome-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..

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 '''Muramyl dipeptide''' is a [[peptidoglycan]] constituent of both [[Gram positive]] and [[Gram negative]] [[bacteria]]. It is composed of [[N-acetylmuramic acid]] linked by its [[lactic acid]] moiety to the [[N-terminus]] of an <small>L</small>-[[alanine]] <small>D</small>-[[isoglutamine]] dipeptide.<ref>{{pmid|12514169}}</ref>
+It can be recognized by the immune system as a PAMP (pathogen associated molecular pattern)and activate the [[NALP3]] [[inflammasome]]  which in turn leads to cytokine activation, especially IL-1α and IL-1β. <ref name="inflammasome">[http://www.ncbi.nlm.nih.gov/pubmed?term=Identification%20of%20bacterial%20muramyl%20dipeptide%20as%20activator%20of%20the%20NALP3%2Fcryopyrin%20inflammasome.%20Curr%20Biol%2014%3A1929%E2%80%931934 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.''.</ref>
 ==See also==