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Muramyl dipeptide

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]

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 Y
3D model (JSmol)
  • Interactive image
ChemSpider
  • 9794910 Y
ECHA InfoCard 100.053.343
  • 5024
MeSH Muramyl+dipeptide
  • 11620162
UNII
  • 2U7S2HVO96 Y
  • DTXSID90897421
  • 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 Y
    Key: BSOQXXWZTUDTEL-QAQREVAFSA-N Y
  • 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
  • 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
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).
Y verify (what is YN ?)

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 edit

References edit

  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. PMID 12514169.
  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 : CB. 14 (21): 1929–1934. doi:10.1016/j.cub.2004.10.027. PMID 15530394.

muramyl, dipeptide, constituent, both, gram, positive, gram, negative, bacteria, composed, acetylmuramic, acid, linked, lactic, acid, moiety, terminus, alanine, isoglutamine, dipeptide, namesiupac, name, acetamido, dihydroxy, hydroxymethyl, oxan, oxypropanoyl,. 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 Muramyl dipeptide NamesIUPAC 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 acidOther names Acetylmuramyl Alanyl IsoglutamineIdentifiersCAS Number 53678 77 6 Y3D model JSmol Interactive imageChemSpider 9794910 YECHA InfoCard 100 053 343IUPHAR BPS 5024MeSH Muramyl dipeptidePubChem CID 11620162UNII 2U7S2HVO96 YCompTox Dashboard EPA DTXSID90897421InChI 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 YKey BSOQXXWZTUDTEL QAQREVAFSA N YInChI 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 s1Key BSOQXXWZTUDTEL QAQREVAFBNSMILES 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 OPropertiesChemical formula C19H32N4O11Molar mass 492 47758Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references 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 1a and IL 1b 2 See also editDipeptide Mifamurtide a synthetic analogue for the treatment of osteosarcomaReferences edit 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 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 CB 14 21 1929 1934 doi 10 1016 j cub 2004 10 027 PMID 15530394 nbsp This article about an organic compound is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Muramyl dipeptide amp oldid 1185531751, wikipedia, wiki, book, books, library,

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