1269619-75-1

Basic information

• Product Name: (6R)-6-allyl 11,15-dibenzyl 2,2,19,19-tetramethyl-4,9,17-trioxo-3,18-dioxa-5,10,16-triazaicosane-6,11,15-tricarboxylate
• CAS NO: 1269619-75-1
• Molecular Weight: 739.863
• Mol File: 1269619-75-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (6R)-6-allyl 11,15-dibenzyl 2,2,19,19-tetramethyl-4,9,17-trioxo-3,18-dioxa-5,10,16-triazaicosane-6,11,15-tricarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (6R)-6-allyl 11,15-dibenzyl 2,2,19,19-tetramethyl-4,9,17-trioxo-3,18-dioxa-5,10,16-triazaicosane-6,11,15-tricarboxylate(1269619-75-1)
• EPA Substance Registry System: (6R)-6-allyl 11,15-dibenzyl 2,2,19,19-tetramethyl-4,9,17-trioxo-3,18-dioxa-5,10,16-triazaicosane-6,11,15-tricarboxylate(1269619-75-1)

Safety Data

• Hazardous Substances Data: 1269619-75-1(Hazardous Substances Data)

Upstream product

• 204251-86-5 (R)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(allyloxy)-5-oxopentanoic acid 
• 13726-84-6 (tert-butoxy)carbonyl-D-glutamic acid 5-tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 922-54-3 2,6-diaminopimelic acid 
• 1269619-48-8 dibenzyl 2-amino-6-((tertbutoxycarbonyl)amino)heptanedioate 
• 98469-29-5 C₁₇H₃₀N₂O₈ 
• 1227363-56-5 dibenzyl 2,6-bis((tert-butoxycarbonyl)amino)heptanedioate 
• 1269619-44-4 (R)-1-allyl 5-tert-butyl 2-((tertbutoxycarbonyl)amino)pentanedioate 
• 1269619-53-5 (5R)-5-allyl 10,14-dibenzyl-1-(9H-fluoren-9-yl)-18,18-dimethyl-3,8,16-trioxo-2,17-dioxa-4,9,15-triazanonadecane-5,10,14-tricarboxylate 

Downstream Products

• 1269619-76-2 (6R)-11,15-dibenzyl 6-undecyl2,2,19,19-tetramethyl-4,9,17-trioxo-3,18-dioxa-5,10,16-triazaicosane-6,11,15-tricarboxylate 
• 1269619-78-4 dibenzyl 2-((tert-butoxycarbonyl)amino)-6-((R)-4-((tert-butoxycarbonyl)amino)-5-oxo-5-(undecylamino)pentanamido)heptanedioate 

Relevant articles and documents

Structure-activity relationships in nucleotide oligomerization domain 1 (Nod1) agonistic γ-glutamyldiaminopimelic acid derivatives

N-Acyl-γ-glutamyldiaminopimelic acid is a prototype ligand for Nod1. We report a detailed SAR of C12-γ-d-Glu-DAP. Analogues with glutaric or γ-aminobutyric acid replacing the glutamic acid show greatly attenuated Nod1-agonistic activity. Substitution of the meso-diaminopimelic (DAP) acid component with monoaminopimelic acid, l- or d-lysine, or cadaverine also results in reduced activity. The free amine on DAP is crucial. However, the N-acyl group on the d-glutamyl residue can be substituted with N-alkyl groups with full preservation of activity. The free carboxylates on the DAP and Glu components can also be esterified, resulting in more lipophilic but active analogues. Transcriptomal profiling showed a dominant up-regulation of IL-19, IL-20, IL-22, and IL-24, which may explain the pronounced Th2-polarizing activity of these compounds and also implicate cell signaling mediated by TREM-1. These results may explain the hitherto unknown mechanism of synergy between Nod1 and TLR agonists and are likely to be useful in designing vaccine adjuvants.