79338-14-0

Basic information

• Product Name: H-D-Glu-OBzl
• Synonyms: 1-Benzyl D-Glutamate;D-Glutamic Acid 1-Benzyl Ester;D-Glutamic Acid 1-Benzyl Ester H-D-Glu-OBzl;alpha-Benzyl D-glutamate;D-Glutamic acid 1-(phenylmethyl) ester;(R)-4-AMino-5-(benzyloxy)-5-oxopentanoic acid;4R)-4-ammonio-5-(benzyloxy)-5-oxopentanoate;D-Glu-OBzl
• CAS NO: 79338-14-0
• Molecular Formula: C₁₂H₁₅NO₄
• Molecular Weight: 237.25
• Product Categories: Amino Acid Benzyl Esters;Amino Acids;Amino Acids (C-Protected);Biochemistry
• Mol File: 79338-14-0.mol
• Article Data: 1

Chemical Properties

• Melting Point: 154 °C
• Boiling Point: 416oC at 760 mmHg
• Flash Point: 205.4oC
• Appearance: Off-white/Solid
• Density: 1.245
• Vapor Pressure: 1.15E-07mmHg at 25°C
• Refractive Index: -28 ° (C=1, 1mol/L HCl)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 4.21±0.10(Predicted)
• CAS DataBase Reference: H-D-Glu-OBzl(CAS DataBase Reference)
• NIST Chemistry Reference: H-D-Glu-OBzl(79338-14-0)
• EPA Substance Registry System: H-D-Glu-OBzl(79338-14-0)

Safety Data

• Hazardous Substances Data: 79338-14-0(Hazardous Substances Data)

Usage

Chemical Properties

White powder

InChI:InChI=1/C12H15NO4/c13-10(6-7-11(14)15)12(16)17-8-9-4-2-1-3-5-9/h1-5,10H,6-8,13H2,(H,14,15)/t10-/m1/s1

Upstream product

• 47376-46-5 D-glutamic acid dibenzyl ester 
• 6893-26-1 D-Glutamic acid 
• 1269619-42-2 (R)-1-benzyl 5-tert-butyl 2-((tert-butoxycarbonyl)amino)pentanedioate 
• 13726-84-6 (tert-butoxy)carbonyl-D-glutamic acid 5-tert-butyl ester 
• 100-51-6 benzyl alcohol 

Downstream Products

• 79337-48-7 N-stearoyl D-Glu(OH)OBzl hydroxysuccinimide ester 
• 142982-02-3 N-<(R)-3-(benzyloxy)tetradecanoyl>-(R)-glutamic acid α-benzyl ester 
• 79337-25-0 α-benzyl caprylyl-D-glutamate 
• 79337-47-6 α-benzyl stearoyl-D-glutamate 
• 678159-24-5 N-tert-butoxycarbonyl-L-alanyl-D-glutamic acid α-benzyl-γ-p-nitrophenyl ester 
• 50515-47-4 N-tert-butoxycarbonyl-L-alanyl-D-glutaminyl-(α-benzyl)-γ-N-ε-benzyloxycarbonyl-L-lysinyl-D-alanyl-D-alanine benzyl ester 
• 79334-23-9 N-stearoyl-γ-D-Glu(α-OBzl)-(L)-Boc-(D)meso-A₂pm 
• 79333-94-1 N-Caprylyl-γ-D-Glu(α-OBzl)-(L)-Boc-(D)meso-A₂pm(D)-NHNHBoc 
• 79327-47-2 caprylyl D-Glu(OSu)OBzl 
• 104091-10-3 (R)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(benzyloxy)-5-oxopentanoic acid 
• 1269619-52-4 (5R)-tribenzyl 1-(9H-fluoren-9-yl)-18,18-dimethyl-3,8,16-trioxo-2,17-dioxa-4,9,15-triazanonadecane-5,10,14-tricarboxylate 
• 1269619-54-6 (5R)-5-benzyl 10,14-diethyl-1-(9H-fluoren-9-yl)-18,18-dimethyl-3,8,16-trioxo-2,17-dioxa-4,9,15-triazanonadecane-5,10,14-tricarboxylate 
• 1269619-55-7 dibenzyl 2-((R)-4-amino-5-(benzyloxy)-5-oxopentanamido)-6-((tert-butoxycarbonyl)amino)heptanedioate 
• 1269619-56-8 (15R)-tribenzyl 2,2-dimethyl-4,12,17-trioxo-3-oxa-5,11,16-triazaoctacosane-6,10,15-tricarboxylate 

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.