62853-36-5

Upstream product

• 18814-49-8 tert-butoxycarbonyl-L-alanyl-D-isoglutamine benzyl ester 
• 66025-93-2 (S)-1-(((R)-1-amino-5-(benzyloxy)-1,5-dioxopentan-2-yl)amino)-1-oxopropan-2-aminium 2,2,2-trifluoroacetate 
• 18800-73-2 benzyl (R)-5-amino-4-((tert-butoxycarbonyl)amino)-5-oxopentanoate 
• 2578-33-8 D-glutamic acid-5-benzyl ester 
• 71811-14-8 D-Glutaminsaeure-α-amid-γ-benzylester 
• 76379-00-5 N-tert-butoxycarbonyl-D-glutamic acid α-p-nitrophenyl-γ-benzyl ester 
• 18800-75-4 D-γ-methyl isoglutamine hydrochloride 
• 6893-26-1 D-Glutamic acid 
• 18800-76-5 Boc-D-Glu(OBzl)-OSu 
• 100-51-6 benzyl alcohol 
• 35793-73-8 N-(tert-butyloxycarbonyl)-γ-benzyl-D-glutamic acid 
• 59524-62-8 L-alanyl-D-isoglutamine benzyl ester hydrochloride 

Downstream Products

• 121788-71-4 1D-(1,2,4/3,5)-2-amino-1,2-N,O-carbonyl-3-O-<(R)-2'-propanoyl-L-alanyl-D-isoglutamine benzylester>-5-C-hydroxymethyl-1,3,4-cyclohexane-triol 
• 121788-67-8 1D-(1,2,4/3,5)-2-acetamido-1,4,5-tri-O-acetyl-3-O-<(R)-2'-propanoyl-L-alanyl-D-isoglutamine benzylester>-1,3,4,5-cyclohexanetetrol 
• 138420-67-4 C₆₂H₉₀N₄O₁₄ 
• 56772-92-0 muramyl dipeptide 
• 45159-25-9 L-alanyl-D-isoglutamine 
• 123418-23-5 N-(2-O--(R)-lactoyl)-L-alanyl-D-glutamine methyl ester 
• 123418-22-4 N-(2-O--(R)-lactoyl)-L-alanyl-D-isoglutamine methyl ester 
• 123418-26-8 N-(2-O--(R)-lactoyl)-L-alanyl-D-glutamine methyl ester 
• 123418-25-7 N-(2-O--(R)-lactoyl)-L-alanyl-D-isoglutamine methyl ester 
• 123418-24-6 N-(2-O--(R)-lactoyl)-L-alanyl-D-isoglutamine benzyl ester 
• 110582-59-7 N-(2-O--(R)-lactoyl)-L-alanyl-D-isoglutamine benzyl ester 
• 1286246-27-2 Nα-[4-chlorocinnamoyl-L-alanyl-D-isoglutaminyl]-L-lysine 

Relevant academic research and scientific papers

Synthesis of muramyl dipeptide isoflavone glycoside

The peracetate of 7-(2-acetamido-2-deoxy-β-D-glucopyranosyloxy)-2- methyl-6-propyl-3′,4′-trimethylenedioxyisoflavone was synthesized under phase-transfer catalysis conditions by quaternary ammonium salts at room temperature and with heating to 50 C in K2CO3 solution (0.18 M):CHCl3. The corresponding glycoside of N-acetylmuramyl-L- alanyl-D-isoglutamine (MDP) was synthesized from the peracetate.

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.

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.

Potential adjuvants for synthetic vaccines. I. Modulators of macrophage activation

The synthesis and biological activities of several glycopeptidolipids derived from muramyl dipeptide (MDP) are described. In combination with gamma interferon (INFγ) MDP derivatives 3c and 3d carrying glycyrrhetinic acid as rigid β-aglycone synergise the

Synthesis and reactions of O-acetylated benzyl alpha-glycosides of 6-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-N-acetylmuramoyl-L- alanyl-D-isoglutamine esters: the base-catalysed isoglutamine in equilibrium glutamine rearrangement in peptidoglycan-re

Condensation of benzyl 2-acetamido-6-O-(2-acetamido-3,4,6-tri-O-acetyl-2- deoxy-3-O-[(R)-1-carboxyethyl]-alpha-D-glucopyranoside (2) and its 4-acetate (4) with L-alanyl-D-isoglutamine benzyl ester via the mixed anhydride method yielded N-(2-O-[benzyl 2-ac

CONVENIENT SYNTHESES OF O-(2-ACETAMIDO-2-DEOXY-β-D-GLUCOPYRANOSYL)-(1->6 AND 4)-N-ACETYLMURAMOYL-L-ALANYL-D-ISOGLUTAMINE

Catalytic hydrogenation of N-(2-O--(R)-lactoyl)-L-alanyl-D-isoglutamine tert-butyl ester (1) afforded N-(2-O-2-acetamido-6-O-(2-acetamido-2-deoxy-β-D-glu

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.