1269620-06-5

Basic information

• Product Name: (R)-benzyl 2-((R)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(benzyloxy)-5-oxopentanamido)-6-((tert-butoxycarbonyl)amino)hexanoate
• CAS NO: 1269620-06-5
• Molecular Weight: 777.915
• Mol File: 1269620-06-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (R)-benzyl 2-((R)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(benzyloxy)-5-oxopentanamido)-6-((tert-butoxycarbonyl)amino)hexanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-benzyl 2-((R)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(benzyloxy)-5-oxopentanamido)-6-((tert-butoxycarbonyl)amino)hexanoate(1269620-06-5)
• EPA Substance Registry System: (R)-benzyl 2-((R)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(benzyloxy)-5-oxopentanamido)-6-((tert-butoxycarbonyl)amino)hexanoate(1269620-06-5)

Safety Data

• Hazardous Substances Data: 1269620-06-5(Hazardous Substances Data)

Upstream product

• 104091-10-3 (R)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(benzyloxy)-5-oxopentanoic acid 
• 1269619-42-2 (R)-1-benzyl 5-tert-butyl 2-((tert-butoxycarbonyl)amino)pentanedioate 
• 79338-14-0 D-glutamic acid 1-benzyl ester 
• 13726-84-6 (tert-butoxy)carbonyl-D-glutamic acid 5-tert-butyl ester 
• 100-51-6 benzyl alcohol 

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.