65706-99-2

Basic information

• Product Name: N-Cbz-D-glutamic acid alpha-benzyl ester
• Synonyms: N-CBZ-D-GLUTAMIC ACID ALPHA-BENZYL ESTER;N-ALPHA-CARBOBENZOXY-D-GLUTAMIC ACID ALPHA-BENZYL ESTER;N-BENZYLOXYCARBONYL-D-GLUTAMIC ACID ALPHA-BENZYL ESTER;N-BENZYLOXYCARBONYL-L-GLUTAMIC ACID ALPHA-BENZYL ESTER;Z-GLU-OBZL;Z-D-GLU-OBZL;Z-D-GLUTAMIC ACID-OBZL;Z-D-GLUTAMIC ACID 1-BENZYL ESTER
• CAS NO: 65706-99-2
• Molecular Formula: C₂₀H₂₁NO₆
• Molecular Weight: 371.38
• EINECS: 2017-001-1
• Product Categories: Glutamic acid [Glu, E];Z-Amino Acids and Derivatives;Z-Amino acid series
• Mol File: 65706-99-2.mol

Chemical Properties

• Melting Point: 98.0 to 102.0 °C
• Boiling Point: 313.2 °C
• Flash Point: 313.2oC
• Appearance: White to off-white/Powder
• Density: 1.268 g/cm³
• Vapor Pressure: 5.72E-15mmHg at 25°C
• Refractive Index: 1.575
• Storage Temp.: −20°C
• Solubility: Soluble in methanol and acetic acid.
• PKA: 4.47±0.10(Predicted)
• BRN: 5305848
• CAS DataBase Reference: N-Cbz-D-glutamic acid alpha-benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-Cbz-D-glutamic acid alpha-benzyl ester(65706-99-2)
• EPA Substance Registry System: N-Cbz-D-glutamic acid alpha-benzyl ester(65706-99-2)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 65706-99-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-Cbz-D-glutamic acid alpha-benzyl ester is used as a reagent for the synthesis of acyl peptides that act as immunostimulants. These immunostimulants are crucial in enhancing the immune response and can be utilized in the development of vaccines and therapeutic agents to combat various diseases and infections.

InChI:InChI=1/C20H21NO6/c22-18(23)12-11-17(19(24)26-13-15-7-3-1-4-8-15)21-20(25)27-14-16-9-5-2-6-10-16/h1-10,17H,11-14H2,(H,21,25)(H,22,23)/t17-/m1/s1

Upstream product

• 71869-80-2 benzyl (R)-(2,6-dioxotetrahydro-2H-pyran-3-yl)carbamate 
• 100-51-6 benzyl alcohol 

Downstream Products

• 1401719-95-6 Cbz-D-Glu(D-Trp-O-5-indanyl)-O-Bzl 
• 1401720-10-2 Cbz-D-Glu(D-Trp-O-cyclohexyl)-O-Bzl 
• 1401719-88-7 Cbz-D-Glu(L-Trp-OCH₂-CO-N(CH₃)2)-OBzl 
• 1401719-33-2 H-D-Glu(D-Trp-O-CH(CH₃)-O-CO-O-cyclohexyl)-OH 
• 1401719-79-6 Cbz-D-Glu(D-Trp-O-CH(CH₃)-O-CO-O-cyclohexyl)-O-Bzl 
• 229305-47-9 Cbz-D-Glu(L-Trp-OH)-OBzl 
• 592532-30-4 (2R)-benzyl 2-(benzyloxycarbonylamino)-5-(tert-butylperoxy)-5-oxopentanoate 
• 79358-64-8 (2S,6R)-2-((R)-4-Benzyloxycarbonylamino-4-carboxy-butyrylamino)-6-tert-butoxycarbonylamino-7-(N'-tert-butoxycarbonyl-hydrazino)-7-oxo-heptanoic acid 
• 79336-02-0 (2S,6R)-6-Amino-2-((R)-4-benzyloxycarbonylamino-4-carboxy-butyrylamino)-6-hydrazinocarbonyl-hexanoic acid 
• 79336-04-2 (2S,6R)-2-Amino-6-((R)-4-benzyloxycarbonylamino-4-carboxy-butyrylamino)-heptanedioic acid 
• 71974-09-9 γ-D-Glutamyl-L-meso-diaminopimelic acid dipeptide 

Relevant articles and documents

Synthesis and Biological Activity of some Fused &β-Lactam Peptidoglycan Analogues

The derivatives (12), (14), (15), (19), and (22), in which a mono- or di-peptide unit is linked to 6-aminopenicillanic acid, have been prepared according to normal synthetic peptide procedures.The structures of the side chains were chosen by analogy with the D-isoglutamyl-L-lysyl sequence present in the cell-wall peptidoglycan of Staphylococcus species.The antibacterial activities of the derivatives were measured and the results are discussed.