71811-14-8

Upstream product

• 18800-73-2 benzyl (R)-5-amino-4-((tert-butoxycarbonyl)amino)-5-oxopentanoate 
• 2578-33-8 D-glutamic acid-5-benzyl ester 
• 35793-73-8 N-(tert-butyloxycarbonyl)-γ-benzyl-D-glutamic acid 
• 76379-00-5 N-tert-butoxycarbonyl-D-glutamic acid α-p-nitrophenyl-γ-benzyl ester 
• 140-11-4 Benzyl acetate 
• 19522-40-8 D-α-glutamine 
• 6893-26-1 D-Glutamic acid 
• 100-51-6 benzyl alcohol 

Downstream Products

• 18814-49-8 tert-butoxycarbonyl-L-alanyl-D-isoglutamine benzyl ester 
• 62853-36-5 L-alanyl-(γ-benzyl ester D-isoglutamine) 
• 56772-92-0 muramyl dipeptide 
• 71811-16-0 (R)-4-(2-Amino-2-methyl-propionylamino)-4-carbamoyl-butyric acid benzyl ester 
• 45159-25-9 L-alanyl-D-isoglutamine 
• 74221-14-0 L-valyl-D-isoglutamine benzyl ester 
• 71921-84-1 O-benzyl-L-seryl-D-isoglutamine benzyl ester 
• 139753-68-7 (R)-4-((2S,3R)-2-Amino-3-benzyloxy-butyrylamino)-4-carbamoyl-butyric acid benzyl ester 
• 76379-11-8 (R)-4-{3-[(R)-2-((4aR,6S,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 
• 66111-90-8 (R)-4-({(S)-1-[(R)-2-((4aR,6S,7R,8R,8aS)-7-Acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionyl]-pyrrolidine-2-carbonyl}-amino)-4-carbamoyl-butyric acid benzyl ester 
• 66111-82-8 (R)-4-{(S)-2-[(R)-2-((4aR,6S,7R,8R,8aS)-7-Acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionylamino]-3-methyl-butyrylamino}-4-carbamoyl-butyric acid benzyl ester 
• 76379-21-0 (R)-4-{(S)-2-[(R)-2-((4aR,6S,7R,8R,8aS)-7-Acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-4-methyl-pentanoylamino]-propionylamino}-4-carbamoyl-butyric acid benzyl ester 
• 66111-85-1 (R)-4-{(2S,3R)-2-[(R)-2-((4aR,6S,7R,8R,8aS)-7-Acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionylamino]-3-benzyloxy-butyrylamino}-4-carbamoyl-butyric acid benzyl ester 
• 66112-14-9 (R)-4-((S)-2-{(R)-2-[(4aR,6S,7R,8R,8aS)-6-Benzyloxy-7-(2-benzyloxy-acetylamino)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-propionylamino}-propionylamino)-4-carbamoyl-butyric acid benzyl ester 

Relevant academic research and scientific papers

Solution-phase synthesis of a muramyl dipeptide analogue MDA

The solution-phase synthesis of a muramyl dipeptide (MDP) analogue of Nα-[4-chlorocinnamoyl-l-alanyl-d-isoglutaminyl]-l-lysine (MDA, 2) is reported that possesses the features of easy feasibility, safety and low cost in large scale of synthesis.

Synthesis of biologically active biotinylated muramyl dipeptides

Muramyl dipeptide (MDP) is believed to interact with an innate immune receptor, Nod2. To identify the cellular receptor for MDP, we have synthesized biotinylated MDP isomers and tested the ability of these compounds to activate Nod2 in a cell-based assay. We found that the modification of MDP does not perturb its ability to activate Nod2. These tagged versions of MDP will be useful to identify the cellular receptor of the immunostimulatory molecules.

Synthesis of some conformationally constrained analogues of muramyl dipeptide (MDP)

Synthesis of three conformationally constrained analogues of MDP, viz AcMur-Δ-Ala-D-isoGln (1), AcMur-Aib-D-isoGln (2) and AcnorMur-Aib-D-isoGln (3) is described. Coupling of the protected carbohydrate derivatives with appropriate dipeptide amines in the

SYNTHESIS AND FAST-ATOM-BOMBARDMENT-MASS SPECTROMETRY OF N-ACETYLMURAMOYL-L-ALANYL-D-ISOGLUTAMINE (MDP)

N-Acetylmuramoyl-L-alanyl-D-isoglutamine (MDP) was synthesized by a series of condensation of appropriate reagents, followed by hydrogenolysis.Each intermediate step resulted in a stable, crystalline product.D-Isoglutamine 4-benzyl ester was condensed with N-(tert-butoxycarbonyl)-L-alanine N-hydroxysuccinimide ester, to give N-(tert-butoxycarbonyl)-L-alanyl-D-isoglutamine benzyl ester.Condensation of L-alanyl-D-isoglutamine benzyl ester with N-acetyl-1-O-benzyl-4,6-O-benzylidenemuramic acid, followed by hydrogenolysis, gave MDP.The synthetic scheme was shown to be capable of producing gram quantities of highly pure MDP, as well as a few of its analogs.The synthetic MDP was characterized by analytical and biological methods, and it was found that the use of fast-atom-bombardment-mass spectrometry may greatly simplify the characterization process.