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Merck

A9519

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

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

Synonyme(s) :

Adjuvant Peptide, Muramyl dipeptide

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A propos de cet article

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

Principaux documents

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Nom du produit

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

InChI key

BSOQXXWZTUDTEL-QAQREVAFSA-N

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

SMILES string

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

assay

≥98% (TLC)

form

powder

technique(s)

ligand binding assay: suitable

color

white

application(s)

cell analysis

storage temp.

−20°C

Quality Level

200

Catégories apparentées

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.

Biochem/physiol Actions

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificats d'analyse (COA)

Lot/Batch Number
0000453044
0000453043
0000453043
0000453044
0000453042

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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
Induction of release of tumor necrosis factor from human monocytes by staphylococci and staphylococcal peptidoglycans.
Timmerman CP
Infection and Immunity, 61(10), 4167-4172 (1993)
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
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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