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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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Properties

Product Name

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

Quality Segment

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

Description

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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Certificates of Analysis (COA)

Lot/Batch Number

0000453044

0000453043