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)
• Beilstein/REAXYS Number: 4220745
• EC Number: 258-696-9
• MDL number: MFCD00077638
• UNSPSC Code: 12352209
• PubChem Substance ID: 24891464
• NACRES: NA.26

Properties

• product name: N-Acetylmuramyl-L-alanyl-D-isoglutamine hydrate, ≥98% (TLC)
• 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

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.

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.

Safety Information

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