A9519

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

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

• Synonym(s): Adjuvant Peptide, Muramyl dipeptide
• 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

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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)