5680-86-4

Basic information

• Product Name: (S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-benzyl ester
• Synonyms: 5-Oxo-5-phenylmethoxy-2-phenylmethoxycarbonylamino-pentanoic acid;CBZ-GLU(OBZL)-OH;CBZ-L-GLUTAMIC ACID G-BENZYL ESTER;BENZYLOXYCARBONYL-L-GLUTAMIC ACID GAMMA-BENZYL ESTER;Z-L-GLUTAMIC ACID GAMMA-BENZYL ESTER;Z-L-GLU(BZL)-OH;Z-GLU(OBZL)-OH;Z-GLUTAMIC ACID(OBZL)-OH
• CAS NO: 5680-86-4
• Molecular Formula: C₂₀H₂₁NO₆
• Molecular Weight: 371.38
• EINECS: 2017-001-1
• Product Categories: AMINOACIDS DERIVATIVES;Z-Amino Acids and Derivatives
• Mol File: 5680-86-4.mol
• Article Data: 4

Chemical Properties

• Melting Point: 74.0 to 78.0 °C
• Boiling Point: 594.3 °C at 760 mmHg
• Flash Point: 313.2 °C
• Appearance: White powder
• Density: 1.268 g/cm³
• Vapor Pressure: 5.72E-15mmHg at 25°C
• Refractive Index: 1.575
• Storage Temp.: Store at RT.
• PKA: 3.79±0.10(Predicted)
• Water Solubility: Soluble in ethanol. Insoluble in water.
• CAS DataBase Reference: (S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-benzyl ester(5680-86-4)
• EPA Substance Registry System: (S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-benzyl ester(5680-86-4)

Safety Data

• Hazardous Substances Data: 5680-86-4(Hazardous Substances Data)

Usage

Chemical Properties

White crystalline powder

Uses

N-Benzyloxycarbonyl-L-glutamic acid 5-benzyl ester is used as pharmaceutical intermediates.

InChI:InChI=1/C20H21NO6/c22-18(26-13-15-7-3-1-4-8-15)12-11-17(19(23)24)21-20(25)27-14-16-9-5-2-6-10-16/h1-10,17H,11-14H2,(H,21,25)(H,23,24)/t17-/m0/s1

Upstream product

• 100-51-6 benzyl alcohol 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 1676-73-9 L-glutamic acid γ-benzyl ester 
• 56-86-0 L-glutamic acid 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 5894-89-3 γ-benzyl α-(4-nitrophenyl) benzyloxycarbonyl-L-glutamate 
• 122701-22-8 N⁶-(O-benzyl-N-benzyloxycarbonyl-L-α-glutamyl)-N²-(toluene-4-sulfonyl)-L-lysine benzyl ester 
• 34312-72-6 N-(O-benzyl-N-benzyloxycarbonyl-L-α-glutamyl)-L-tyrosine benzyl ester 
• 139937-97-6 Z-L-isoGln-OBzl 
• 108039-06-1 O-benzyl-N-benzyloxycarbonyl-α-glutamyl=>tyrosyl=>tyrosyl=>tyrosine ethyl ester 
• 7540-08-1 benzyloxycarbonyl-γ-benzyl-α-L-glutamyl-D-glutamic acid dibenzyl ester 
• 6922-66-3 benzyloxycarbonyl-γ-benzyl-α-L-glutamyl-L-glutamic acid dibenzyl ester 
• 96467-84-4 N-(O-benzyl-N-benzyloxycarbonyl-L-α-glutamyl)-D-alanine benzyl ester 
• 96467-84-4 N-(O-benzyl-N-benzyloxycarbonyl-L-α-glutamyl)-L-alanine benzyl ester 
• 3190-71-4 5-benzyl L-glutamate N-carboxyanhydride 
• 6402-94-4 (S)-4-Benzyloxycarbonylamino-4-((S)-1-carboxy-2-hydroxy-ethylcarbamoyl)-butyric acid benzyl ester 
• 80963-13-9 Z-Glu(OBzl)-OCH₂CH₃ 
• 80963-13-9 (R)-2-Benzyloxycarbonylamino-pentanedioic acid 5-benzyl ester 1-ethyl ester 
• 67413-34-7 O^γ-benzyl-N^α-benzyloxycarbonylglutamic acid succinimidyl ester 

Relevant articles and documents

Preparation method of N-fluorenylmethoxycarbonyl-gamma-(S-triphenylmethyl-cysteamine)-L-glutamic acid

The invention provides a preparation method of N-fluorenylmethoxycarbonyl-gamma-(S-triphenylmethyl-cysteamine)-L-glutamic acid. The preparation method mainly solves the technical problems of complexity, long period, high cost, and low yield of an original process, and comprises the following steps: (1) preparing N-fluorenylmethoxycarbonyl-L-glutamic acid; (2) preparing N-fluorenylmethoxycarbonyl-L-glutamic acid-1-benzyl ester; (3) preparing S-triphenylmethyl cysteamine; (4) preparing N-fluorenylmethoxycarbonyl-gamma-(S-triphenylmethyl-cysteamine)-L-glutamic acid-alpha-benzyl ester; and (5) preparing N-fluorenylmethoxycarbonyl-gamma-(S-triphenylmethyl-cysteamine)-L-glutamic acid. The method is rapid, high in yield and simple in separation and purification, and the used solvent is environment-friendly and is suitable for mass production.

Glutamyl adenylate analogues are inhibitors of glutamyl-tRNA synthetase

Glutamol adenylate 10 was a competitive inhibitor (K(i) = 3 μM) of glutamyl-tRNA synthetase from Escherichia coli. The N6-benzoyl adenine derivative 9 was also an inhibitor (K(i) ~ 60 μM). Replacement of adenine by other bases (purine, cytosine