53678-77-6

Usage

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

• 93218-76-9 N-acetyl-1-O-benzyl-4,6-O-benzylidenemuramoyl-L-alanyl-D-idoglutamine benzyl ester 
• 87173-14-6 (R)-4-{(S)-2-[(R)-2-((2R,4aR,7R,8R,8aS)-7-Acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionylamino]-propionylamino}-4-carbamoyl-butyric acid benzyl ester 
• 59524-62-8 L-alanyl-D-isoglutamine benzyl ester hydrochloride 
• 78062-11-0 1-O-benzyl-N-acetyl-muramyl-L-alanyl-D-isoglutamine 
• 78246-81-8 benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 13343-62-9 benzyl 2-acetamido-2-deoxy-α-D-glucopyranoside 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 112897-97-9 (E)-3-(3,4-difluorophenyl)acrylic acid 
• 459-32-5 (E)-4-fluorocinnamic acid 
• 174603-37-3 3-(2-chloro-4-fluorophenyl)-2-propenoic acid 
• 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 

Downstream Products

• 87137-44-8 C₄₂H₄₂N₈O₁₇^(2-)*2Na⁽¹⁺⁾ 
• 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 

Relevant academic research and scientific papers

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.

Synthesis of Diverse N-Substituted Muramyl Dipeptide Derivatives and Their Use in a Study of Human NOD2 Stimulation Activity

A flexible synthetic strategy toward the preparation of diverse N-substituted muramyl dipeptides (N-substituted MDPs) from different protected monosaccharides is described. The synthetic MDPs include N-acetyl MDP and N-glycolyl MDP, known NOD2 ligands, and this methodology allows for structural variation at six positions, including the muramic acid, peptide, and N-substituted moieties. The capacity of these molecules to activate human NOD2 in the innate immune response was also investigated. It was found that addition of the methyl group at the C1 position of N-glycolyl MDP significantly enhanced the NOD2 stimulating activity.

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.

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).

CONTROL OF SPORE GERMINATION

Provided are compositions and methods for treating bacterial infections. It is demonstrated herein that bacteria cell wall materials stimulate germination of spores of Gram-positive bacteria, and that such activity requires Ser/Thr kinase PrkC. By modulating one or both, spores (which can be antibiotic resistant) can be stimulated or inhibited from germination, which can be exploited in various methods of therapeutic treatment. Also provided is a method of modulating germination of a spore of a Gram-positive bacterium. Also provided is a method of decontaminating an environment.

ONE-PACK TYPE COATING MATERIAL FOR TOOTH SURFACE

[Problems] To provide a one-package type tooth surface coating material that is capable of forming, on the surface of a tooth, a cured film having not only a very high strength of adhesion to the tooth surface but also excellent properties such as long-term adhesion, long-term durability, dentinal tubule occlusion and aesthetic appearance, and that has excellent storage stability and can be stored in the form of one package. [Means for Solution] A one-package type tooth surface coating material comprising (A) a polymerizable monomer component containing not less than 5% by mass of an acidic group-containing polymerizable monomer; (B) polyvalent metal ions; (C) a volatile water-soluble organic solvent; (D) water; and (E) an effective amount of a photopolymerization initiator; the amount of the polyvalent metal ions (B) and the amount of the volatile water-soluble organic solvent (C) satisfying a specific relationship.

Organophosphorus compounds for dental polymerizable compositions

An organic phosphate compound having at least one radically polymerizable double bond, at least one phosphate residue having one or two hydroxyl groups, and at least one hydrocarbon group having 4 or more carbon atoms in a molecule, wherein a 10% by weight methanol solution of the organic phosphate compound has an electric conductivity at 25° C. of 0.5 mS/cm or less, and/or the organic phosphate compound has a light transmittance at 455 nm of 90% or more; a process for preparing the organic phosphate compound; a dental polymerizable composition comprising (a) the organic phosphate compound and (b) a polymerizable monomer capable of copolymerizing with the organic phosphate compound.

VINYL ETHER DERIVATIVES

Processes for the manufacture of vinyl ether derivatives, e.g., methoxydihydropyran, are disclosed which comprise reacting acetylene and a lower alcohol, e.g., methanol, to form a vinyl alkyl ether, e.g., vinyl methyl ether, reacting the vinyl alkyl ether so produced with an alpha , beta -unsaturated carbonylic compound, e.g., acrolein, in the presence of the lower alcohol to preferably enhance the conversion of the vinyl alkyl ether to the vinyl ether derivative. In one aspect of the invention, the vinyl ether derivative is methoxydihydropyran which is subjected to hydrolysis to form glutaraldehyde.

Polymeric immunological adjuvants

Adjuvants for enhancing the immune response to an antigen are provided comprising the adjuvant incorporated into a lipid layer where the adjuvant is covalently or non-covalently involved in a polymeric system. Conveniently, the adjuvant may be conjugated to a polymerizable group and co-polymerized with a water-soluble and/or amphiphilic polymerizable monomer or combined with a polymerized amphiphile. The adjuvant and antigen may then be administered to a mammalian host to obtain enhanced immune response.