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A9519

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

Name: N-Acetylmuramyl-<SC>L</SC>-alanyl-<SC>D</SC>-isoglutamine hydrate
Brand: SIGMA

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

Synonym(s):

Adjuvant Peptide, Muramyl dipeptide

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About This Item

Empirical Formula (Hill Notation):

C₁₉H₃₂N₄O₁₁ · xH₂O

CAS Number:

53678-77-6

Molecular Weight:

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

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Product Name

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

Quality Level

200

assay

≥98% (TLC)

form

powder

technique(s)

ligand binding assay: suitable

color

white

application(s)

cell analysis

storage temp.

−20°C

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

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

InChI key

BSOQXXWZTUDTEL-QAQREVAFSA-N

Related Categories

Biochemicals

Cell Culture Supplements & Reagents

Amino Acids – Building Blocks of Life Science

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

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.

Enhances antigenicity of weak antigens, increasing antibody titer.

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.

Storage Class

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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NOD2-mediated innate immune signaling regulates the eicosanoids in atherosclerosis.

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

Key structures of bacterial peptidoglycan and lipopolysaccharide triggering the innate immune system of higher animals: chemical synthesis and functional studies.

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

N-glycolylated peptidoglycan contributes to the immunogenicity but not pathogenicity of Mycobacterium tuberculosis.

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

Endosomes are specialized platforms for bacterial sensing and NOD2 signalling.

Norihiro Nakamura et al.

Nature, 509(7499), 240-244 (2014-04-04)

The detection of microbial pathogens involves the recognition of conserved microbial components by host cell sensors such as Toll-like receptors (TLRs) and NOD-like receptors (NLRs). TLRs are membrane receptors that survey the extracellular environment for microbial infections, whereas NLRs are

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)

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Global Trade Item Number

SKU	GTIN
A9519-25MG	04061833402764
A9519-1MG	04061826282946
A9519-10MG	04061832819112
A9519-5MG	04061833402795

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