62928-83-0

Basic information

• Product Name: 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
• Synonyms: 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
• CAS NO: 62928-83-0
• Molecular Weight: 672.733
• Mol File: 62928-83-0.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 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(CAS DataBase Reference)
• NIST Chemistry Reference: 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(62928-83-0)
• EPA Substance Registry System: 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(62928-83-0)

Safety Data

• Hazardous Substances Data: 62928-83-0(Hazardous Substances Data)

Upstream product

• 35793-73-8 N-(tert-butyloxycarbonyl)-γ-benzyl-D-glutamic acid 
• 78246-81-8 benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 69323-69-9 benzyl (R)-4-((S)-2-((R)-2-(((4aR,6S,7R,8R,8aS)-7-acetamido-6-(benzyloxy)-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)propanamido)propanamido)-5-amino-5-oxopentanoate 
• 80143-17-5 (R)-1-amino-5-(benzyloxy)-1,5-dioxopentan-2-aminium 2,2,2-trifluoroacetate 
• 18800-73-2 benzyl (R)-5-amino-4-((tert-butoxycarbonyl)amino)-5-oxopentanoate 
• 55297-72-8 (R)-5-amino-4-((tert-butoxycarbonyl)amino)-5-oxopentanoic acid 
• 19522-39-5 (R)-5-amino-4-(((benzyloxy)carbonyl)amino)-5-oxopentanoic acid 
• 63648-73-7 N-benzyloxycarbonyl-D-glutamic acid 
• 6893-26-1 D-Glutamic acid 
• 69323-67-7 (R)-2-(((4aR,6S,7R,8R,8aS)-7-acetamido-6-(benzyloxy)-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)propanoic acid 
• 66025-93-2 (S)-1-(((R)-1-amino-5-(benzyloxy)-1,5-dioxopentan-2-yl)amino)-1-oxopropan-2-aminium 2,2,2-trifluoroacetate 
• 66026-10-6 N-((4aR,6S,7R,8R,8aS)-6-(benzyloxy)-8-hydroxy-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-7-yl)acetamide 
• 13343-62-9 benzyl 2-acetamido-2-deoxy-α-D-glucopyranoside 

Downstream Products

• 56772-92-0 muramyl dipeptide 
• 78062-11-0 1-O-benzyl-N-acetyl-muramyl-L-alanyl-D-isoglutamine 
• 128726-70-5 N-(2-O--D-lactoyl)-L-alanyl-D-isoglutamine benzyl ester trifluoroacetate 
• 128747-55-7 N-(2-O--D-lactoyl)-L-alanyl-D-isoglutamine benzyl ester trifluoroacetate 
• 73348-28-4 (S)-Pyrrolidine-1,2-dicarboxylic acid 2-((2R,3S,4R,5R,6S)-5-acetylamino-6-benzyloxy-4-{1-[(S)-1-((R)-3-benzyloxycarbonyl-1-carbamoyl-propylcarbamoyl)-ethylcarbamoyl]-ethoxy}-3-hydroxy-tetrahydro-pyran-2-ylmethyl) ester 1-benzyl ester 
• 80143-19-7 11-Benzyloxycarbonylamino-undecanoic acid (2R,3S,4R,5R,6S)-5-acetylamino-6-benzyloxy-4-{1-[1-((R)-3-benzyloxycarbonyl-1-carbamoyl-propylcarbamoyl)-1-methyl-ethylcarbamoyl]-ethoxy}-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester 
• 141540-27-4 6-(4-Nitro-9-oxo-9,10-dihydro-acridin-1-ylamino)-hexanoic acid (2R,3S,4R,5R,6R)-5-acetylamino-6-benzyloxy-4-{(S)-1-[(S)-1-((R)-3-benzyloxycarbonyl-1-carbamoyl-propylcarbamoyl)-ethylcarbamoyl]-ethoxy}-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester 
• 141540-26-3 (R)-4-[(S)-2-((S)-2-{(2R,3R,4R,5S,6R)-3-Acetylamino-2-benzyloxy-5-hydroxy-6-[4-(4-nitro-9-oxo-9,10-dihydro-acridin-1-ylamino)-butyryloxymethyl]-tetrahydro-pyran-4-yloxy}-propionylamino)-propionylamino]-4-carbamoyl-butyric acid benzyl ester 
• 141523-42-4 (R)-4-[(S)-2-((S)-2-{(2R,3R,4R,5S,6R)-3-Acetylamino-2-benzyloxy-5-hydroxy-6-[3-(1-nitro-acridin-9-ylamino)-propionyloxymethyl]-tetrahydro-pyran-4-yloxy}-propionylamino)-propionylamino]-4-carbamoyl-butyric acid benzyl ester 
• 141540-28-5 (R)-4-[(S)-2-((S)-2-{(2R,3R,4R,5S,6R)-3-Acetylamino-6-[3-(acridin-9-ylamino)-propionyloxymethyl]-2-benzyloxy-5-hydroxy-tetrahydro-pyran-4-yloxy}-propionylamino)-propionylamino]-4-carbamoyl-butyric acid benzyl ester 
• 141523-43-5 (R)-4-[(S)-2-((S)-2-{(2R,3R,4R,5S,6R)-3-Acetylamino-2-benzyloxy-6-[3-(6-chloro-2-methoxy-acridin-9-ylamino)-propionyloxymethyl]-5-hydroxy-tetrahydro-pyran-4-yloxy}-propionylamino)-propionylamino]-4-carbamoyl-butyric acid benzyl ester 

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.

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 combination of 6-deoxy-6-mycoloylamino-α,α-trehalose and N-acetyl-6-O-(aminoacyl)muramoyl dipeptide

6-Deoxy-6-mycoloylamino-α,α-trehalose, a biologically active derivative of 6,6′-di-O-mycoloyl-α,α-trehalose (TDM), and N-acetyl-6-O-(aminoacyl)-muramoyl dipeptide (MDP) were joined chemically by a succinic acid unit. The compounds synthesized showed activ