53678-77-6

Basic information

• Product Name: N-ACETYLMURAMYL-L-ALANYL-D-ISOGLUTAMINE
• Synonyms: acetylmuramyl-alanyl-isoglutamine;n(sup2)-(n-(n-acetylmuramoyl)-l-alanyl)-d-alpha-glutamin;n(sup2)-(n-(n-acetylmuramoyl)-l-alanyl)-d-alpha-glutamine;N-AC-MURAMYL-ALA-D-GLU-NH2;N-AC-MURAMYL-ALA-D-GLU-NH2 2H2O;N-ACETYL-MURAMYL-L-ALA-D-ISOGLN;N-ACETYLMURAMYL-L-ALA-D-ISOGLUTAMINE;N-ACETYLMURAMYL-L-ALANYL-D-ISOGLUTAMINE
• CAS NO: 53678-77-6
• Molecular Formula: C₁₉H₃₂N₄O₁₁
• Molecular Weight: 492.48
• EINECS: 258-696-9
• Mol File: 53678-77-6.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 1023.75 °C at 760 mmHg
• Flash Point: 572.943 °C
• Appearance: /
• Density: 1.45 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.578
• Storage Temp.: −20°C
• Solubility: H2O: 10 mg/mL, clear, colorless
• PKA: 4.44±0.10(Predicted)
• Merck: 13,6329
• BRN: 4220745
• CAS DataBase Reference: N-ACETYLMURAMYL-L-ALANYL-D-ISOGLUTAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-ACETYLMURAMYL-L-ALANYL-D-ISOGLUTAMINE(53678-77-6)
• EPA Substance Registry System: N-ACETYLMURAMYL-L-ALANYL-D-ISOGLUTAMINE(53678-77-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: MA2275260
• F: 10
• Hazardous Substances Data: 53678-77-6(Hazardous Substances Data)

Usage

Description

N-ACETYLMURAMYL-L-ALANYL-D-ISOGLUTAMINE, also known as MurNAc-L-Ala-D-iGln or NAM, is a small peptide derived from the bacterial cell wall. It is a component of peptidoglycan, which is essential for the structural integrity of bacterial cells. This molecule has immunomodulatory properties and has been extensively studied for its potential applications in various fields.

Uses

Used in Immunological Applications:
N-ACETYLMURAMYL-L-ALANYL-D-ISOGLUTAMINE is used as an immunological adjuvant for enhancing the immune response to vaccines. It stimulates the immune system by activating macrophages and other immune cells, leading to the production of cytokines and other immune mediators.
Used in Staphylococcal Cell Wall Preparation:
N-ACETYLMURAMYL-L-ALANYL-D-ISOGLUTAMINE is used as a component in staphylococcal cell wall preparation to induce the release of Tumor Necrosis Factor (TNF) from human monocytes. This release of TNF can help in the immune response against bacterial infections, particularly those caused by Staphylococcus aureus.
Used in Pharmaceutical Industry:
N-ACETYLMURAMYL-L-ALANYL-D-ISOGLUTAMINE is used as a potential therapeutic agent for various diseases, including cancer and bacterial infections. Its immunomodulatory properties make it a promising candidate for the development of new drugs and treatment strategies.
Used in Research and Development:
N-ACETYLMURAMYL-L-ALANYL-D-ISOGLUTAMINE is used as a research tool for studying the mechanisms of bacterial cell wall synthesis, immune system activation, and the development of new vaccines and immunotherapies.

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.

InChI:InChI=1/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

Upstream product

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• 78246-81-8 benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
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• 73089-68-6 benzyl 2-acetamido-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-α-D-glucopyranoside 
• 62928-83-0 benzyl (R)-4-((S)-2-((R)-2-(((2S,3R,4R,5S,6R)-3-acetamido-2-(benzyloxy)-5-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)oxy)propanamido)propanamido)-5-amino-5-oxopentanoate 
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• 312693-55-3 (E)-3-(4-chloro-2-fluoro-phenyl)prop-2-enoic acid 
• 94977-52-3 2,4-Difluorocinnamic acid 
• 1866-39-3 trans-p-methylcinnamic acid 
• 7400-08-0 p-Coumaric Acid 
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Downstream Products

• 1856-93-5 (R)-2-(((3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)oxy)propanoic acid 
• 45159-25-9 L-alanyl-D-isoglutamine 
• 87137-44-8 C₄₂H₄₂N₈O₁₇^(2-)*2Na⁽¹⁺⁾ 

Relevant articles and documents

Further Insights on Structural Modifications of Muramyl Dipeptides to Study the Human NOD2 Stimulating Activity

A series of muramyl dipeptide (MDP) analogues with structural modifications at the C4 position of MurNAc and on the d-iso-glutamine (isoGln) residue of the peptide part were synthesized. The C4-diversification of MurNAc was conveniently achieved by using CuAAC click strategy to conjugate an azido muramyl dipeptide precursor with structurally diverse alkynes. d-Glutamic acid (Glu), replaced with isoGln, was applied for the structural diversity through esterification or amidation of the carboxylic acid. In total, 26 MDP analogues were synthesized and bio-evaluated for the study of human NOD2 stimulation activity in the innate immune response. Interestingly, MDP derivatives with an ester moiety are found to be more potent than reference compound MDP itself or MDP analogues containing an amide moiety. Among the varied lengths of the alkyl chain in ester derivatives, the MDP analogue bearing the d-glutamate dodecyl (C12) ester moiety showed the best NOD2 stimulation potency.

Chemical synthesis and anti-tumor and anti-metastatic effects of dual functional conjugate

The present invention discloses chemical synthesis, anti-tumor and anti-metastatic effects of a dual functional conjugate as shown by formula I. Specifically, paclitaxel or docetaxol is linked with muramyl dipeptide derivative to form a conjugate, thus dual anti-tumor and anti-metastatic effects are achieved by combination of chemotherapy and immunotherapy. The present invention also discloses that paclitaxel or docetaxol and muramyl dipeptide derivative conjugate is synthesized by combination of solid-phase and solution-phase synthesis, and said conjugate can be used in manufacture of anti-tumor medicaments as proved by reliable bioassays.

DENTAL FILLING REPAIR KIT

Provided is a filling/restoring material, including a photopolymerization initiator of a quaternary system formed by combining an a-diketone compound, an aliphatic amine compound, an aromatic amine compound, and a photoacid generator, in which even when the filling/restoring material is filled and cured on a cured layer of a dental adhesive material including a radical-polymerizable monomer having an acidic group, the filling/restoring material undergoes sufficient curing up to a contact interface between the filling/restoring material and the cured layer, thereby providing high adhesive strength stably. Also provided is a dental filling/restoration kit, including: a filling/restoring material (A) including: a polymerizable monomer having no acidic group (I); a basic inorganic material (II); and a photopolymerization initiator (III) formed by at least combining: an a-diketone compound (i); an aliphatic amine compound (ii); an aromatic amine compound (iii) ; and a photoacid generator (iv); and an adhesive material (B), which is used for adhesion between a tooth and the filling/restoring material by curing the adhesive material before filling the filling/restoring material, the adhesive material including: a polymerizable monomer including a polymerizable monomer having an acidic group (I); and a polymerization initiator (II).