N-acetyl-beta-glucosaminyl-N-acetylmuramyl-alanylisoglutamine

Base Information

• Chemical Name: N-acetyl-beta-glucosaminyl-N-acetylmuramyl-alanylisoglutamine
• CAS No.: 70280-03-4
• Molecular Formula: C27H45N5O16
• Molecular Weight: 695.6701
• DSSTox Substance ID: DTXSID70990489
• Wikidata: Q21097973
• Mol file: 70280-03-4.mol

Synonyms:acetylglucosaminyl-AMAIG;D-alpha-Glutamine, N2-(N-(2-(acetylamino)-4-O-(2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl)-2-deoxymuramoyl)-L-alanyl)-;GlcNAc-AMAIG;N-acetyl-beta-D-glucosaminyl-N-acetylmuramyl-L-alanyl-D-isoglutamine;N-acetyl-beta-glucosaminyl-N-acetylmuramyl dipeptide;N-acetyl-beta-glucosaminyl-N-acetylmuramyl-alanylisoglutamine;N-acetyl-beta-glucosaminyl-N-AcMu-Ala-iso-Gln;N-acetylglucosaminyl (beta1-4) acetylmuramyl-L-alanyl-D-isoglutamine;N-acetylglucosaminyl (beta1-4)-muramyl dipeptide;N-acetylglucosaminyl-mdp

Chemical Property of N-acetyl-beta-glucosaminyl-N-acetylmuramyl-alanylisoglutamine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1270.1°Cat760mmHg
• Flash Point: 721.9°C
• Density: 1.47g/cm³
• Storage Temp.: −20°C
• XLogP3: -6.2
• Hydrogen Bond Donor Count: 11
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 20
• Exact Mass: 695.28613036
• Heavy Atom Count: 48
• Complexity: 1140

Purity/Quality:

99% ^*data from raw suppliers

N-?Acetyl-?β-?D-?glucosaminyl-?N-?acetylmuramyl-?L-?alanyl-?D-?isoglutamine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37

MSDS Files:

Useful:

• Canonical SMILES: CC(C(=O)NC(CCC(=O)O)C(=O)N)NC(=O)C(C)OC(C(C=O)NC(=O)C)C(C(CO)O)OC1C(C(C(C(O1)CO)O)O)NC(=O)C
• Isomeric SMILES: C[C@@H](C(=O)N[C@H](CCC(=O)O)C(=O)N)NC(=O)[C@@H](C)O[C@H]([C@H](C=O)NC(=O)C)[C@@H]([C@@H](CO)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)NC(=O)C
• Description: N-acetyl-β-D-glucosaminyl-( 1→4)-N-acetylmuramyl-L-alanyl-D-isoglutamine was launched in Russia for hospital-related infections, psoriasis, cervical precancerous lesions and ophthalmic keratitis caused by herpes. It was found to be less pyrogenic than MDP, the minimally active component of Freund's complete adjuvant. While chemical synthesis is possible, a less laborious method (3 steps) involves the enzymatic degradation of a bacterial peptidoglycan. GDMP is orally active with a low toxicity that acts as an adjuvant to highly purified protein antigens to stimulate the induction of CD8* T-cell response. It was also able to reduce the levels of TNF-α, IL-1α and hypoglycemia induced by LPS administration and to inhibit systemic response to endotoxin.
• Uses: N-?Acetyl-?β-?D-?glucosaminyl-?N-?acetylmuramyl-?L-?alanyl-?D-?isoglutamine acts as an immunnomodulator or immunostimulant in the treatment of various auto-immune diseases.