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A9519

Sigma-Aldrich

N-Acetylmuramyl-L-alanyl-D-isoglutamine hydrate

≥98% (TLC), suitable for ligand binding assays

Synonyme(s) :

Adjuvant Peptide, Muramyl dipeptide

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About This Item

Formule empirique (notation de Hill):
C19H32N4O11 · xH2O
Numéro CAS:
53678-77-6
Poids moléculaire :
492.48 (anhydrous basis)
Numéro Beilstein :
4220745
Numéro CE :
258-696-9
Numéro MDL:
MFCD00077638
Code UNSPSC :
12352209
ID de substance PubChem :
24891464
Nomenclature NACRES :
NA.26

product name

N-Acetylmuramyl-L-alanyl-D-isoglutamine hydrate, ≥98% (TLC)

Niveau de qualité

200

Pureté

≥98% (TLC)

Forme

powder

Technique(s)

ligand binding assay: suitable

Couleur

white

Application(s)

cell analysis

Température de stockage

−20°C

Chaîne SMILES 

C[C@H](NC(=O)[C@@H](C)O[C@H]1[C@H](O)[C@@H](CO)OC(O)[C@@H]1NC(C)=O)C(=O)N[C@H](CCC(O)=O)C(N)=O

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

Clé InChI

BSOQXXWZTUDTEL-QAQREVAFSA-N

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Catégories apparentées

Amino Acid Sequence

MurNAc-Ala-Agn

Application

N-Acetylmuramyl-L-alanyl-D-isoglutamine hydrate has been used in staphylococcal cell wall preparation to induce the release of TNF from human monocytes.

Actions biochimiques/physiologiques

Enhances antigenicity of weak antigens, increasing antibody titer.
Muramyl peptides are monomeric components that make up the bacterial cell wall peptidoglycan. It is generally produced by mammalian macrophages, as an immune response in the breakdown of bacterial cell wall. MDP promotes the production of interleukin-1 and tumor necrosis factor (TNF), which increase slow-wave sleep.
N-Acetylmuramyl-L-alanyl-D-isoglutamine (MDP, muramyl dipeptide), a neurotrophic and immunomodulatory factor related to bacterial peptidoglycans, is used as an immune modulation factor that enhances immune response and to study neural development.

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

S Ammann et al.
Clinical and experimental immunology, 176(3), 394-400 (2014-03-13)
X-linked inhibitor of apoptosis (XIAP) deficiency, caused by mutations in BIRC4, is an immunodeficiency associated with immune dysregulation and a highly variable clinical presentation. Current diagnostic screening tests such as flow cytometry for XIAP expression or lymphocyte apoptosis assays have
Hui-Qing Liu et al.
Arteriosclerosis, thrombosis, and vascular biology, 33(9), 2193-2201 (2013-07-23)
The activity of eicosanoid pathways is critical to the inflammatory and immune responses that are associated with the progression of atherosclerosis. Yet, the signals that regulate these pathways are poorly understood. Here, we address whether the innate immune signals of
Shoichi Kusumoto et al.
Proceedings of the Japan Academy. Series B, Physical and biological sciences, 86(4), 322-337 (2010-05-01)
Chemistry-based investigation is reviewed which led to identification of the active entities responsible for the immunostimulating potencies of peptidoglycan and lipopolysaccharide. Though these glycoconjugates which ubiquitously occur in wide range of bacteria as the essential components of their cell envelopes
Muramyl dipeptide and IL-1 effects on sleep and brain temperature after inhibition of serotonin synthesis.
Imeri L
The American Journal of Physiology, 273(5 Pt 2), R1663-R1668 (1997)
Jesse M Hansen et al.
The Journal of infectious diseases, 209(7), 1045-1054 (2013-11-23)
Mycobacteria produce an unusual, glycolylated form of muramyl dipeptide (MDP) that is more potent and efficacious at inducing NOD2-mediated host responses. We tested the importance of this modified form of MDP in Mycobacterium tuberculosis by disrupting the gene, namH, responsible
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