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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/09/26 11:14:57」(JST)

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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[edit]

^ 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. edit
^ 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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English Journal

Synthesis of Diverse N-Substituted Muramyl Dipeptide Derivatives and Their Use in a Study of Human NOD2 Stimulation Activity.

Chen KT1,2, Huang DY3, Chiu CH1, Lin WW4, Liang PH5, Cheng WC6.
Chemistry (Weinheim an der Bergstrasse, Germany).Chemistry.2015 Aug 17;21(34):11984-8. doi: 10.1002/chem.201501557. Epub 2015 Jul 16.
A flexible synthetic strategy toward the preparation of diverse N-substituted muramyl dipeptides (N-substituted MDPs) from different protected monosaccharides is described. The synthetic MDPs include N-acetyl MDP and N-glycolyl MDP, known NOD2 ligands, and this methodology allows for structural vari
PMID 26226896

Reconstituted AIM2 inflammasome in cell-free system.

Kaneko N1, Ito Y1, Iwasaki T1, Takeda H2, Sawasaki T2, Migita K3, Agematsu K4, Kawakami A5, Morikawa S1, Mokuda S1, Kurata M1, Masumoto J6.
Journal of immunological methods.J Immunol Methods.2015 Aug 8. pii: S0022-1759(15)30031-4. doi: 10.1016/j.jim.2015.08.004. [Epub ahead of print]
Absent in melanoma 2 (AIM2) is an intracellular pattern-recognition receptor, which is a member of the PYHIN protein family, consisting of a PYD domain and an IFN-inducible nuclear localization (HIN) domain. AIM2 is reported to oligomerize with adaptor protein ASC upon sensing bacterial and viral cy
PMID 26259507

DUOX2 promotes the elimination of the Klebsiella pneumoniae strain K5 from T24 cells through the reactive oxygen species pathway.

Lu H1, Wu Q2, Yang H1.
International journal of molecular medicine.Int J Mol Med.2015 Aug;36(2):551-8. doi: 10.3892/ijmm.2015.2234. Epub 2015 Jun 3.
Dual oxidase 2 (DUOX2) plays a major role in host defense in intestinal and airway epithelial cells through the reactive oxygen species (ROS) pathway. Klebsiella pneumoniae is a uropathogen that causes urinary tract infections. It is not known whether DUOX2 plays a role in host defense in bladder
PMID 26046128

Japanese Journal

A synthetic NOD2 agonist, muramyl dipeptide (MDP)-Lys (L18) and IFN-β synergistically induce dendritic cell maturation with augmented IL-12 production and suppress melanoma growth

Journal of dermatological science 62(2), 107-115, 2011-05-01
NAID 10030891164

Sarcoidosis and Autoinflammation

Inflammation and Regeneration 31(1), 66-71, 2011
NAID 130004943773

自然免疫系を始動するバクテリア複合糖質の合成と機能研究

Trends in glycoscience and glycotechnology 22(125), 107-118, 2010-05-31
NAID 10027508280

Related Pictures

★リンクテーブル★

リンク元	「ムラミルジペプチド」「acetylmuramyl-alanyl-isoglutamine」「muramyldipeptide」

「ムラミルジペプチド」

Muramyl dipeptide
	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
PubChem	11620162
ChemSpider	9794910
MeSH	Muramyl+dipeptide
Jmol-3D images	Image 1
	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 ;
	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 ;
Properties
Molecular formula	C19H32N4O11
Molar mass	492.47758
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references