7300-59-6

Basic information

• Product Name: GAMMA-L-GLUTAMYL-4-NITROANILIDE
• Synonyms: ^y-L-Glutamyl-4-nitroanilide, 98+%;L-gamma-Glutamyl-p-nitroanilide monohydrate,98%;gamma-L-Glutamyl-4-nitroanilide, 98+%;L-γ-GlutaMyl-p-nitroanilide Monohydrate;(S)-2-AMino-5-((4-nitrophenyl)aMino)-5-oxopentanoic acid;L-GlutaMy-4-nitroanilide MoMhydrate;GaMMa - L - glutaMine paranitroaniline a hydrate;L-gaMMa- glutaMyl - on - nitroaniline
• CAS NO: 7300-59-6
• Molecular Formula: C₁₁H₁₃N₃O₅
• Molecular Weight: 267.24
• EINECS: 230-748-5
• Mol File: 7300-59-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 185-188°C
• Boiling Point: 590.6 °C at 760 mmHg
• Flash Point: 311 °C
• Appearance: cream coloured to light yellow powder
• Density: 1.463
• Refractive Index: 32 ° (C=2, 0.5mol/L HCl)
• Storage Temp.: 2-8°C
• Solubility: Aqueous Acid (Slightly)
• PKA: 2.21±0.10(Predicted)
• BRN: 2818758
• CAS DataBase Reference: GAMMA-L-GLUTAMYL-4-NITROANILIDE(CAS DataBase Reference)
• NIST Chemistry Reference: GAMMA-L-GLUTAMYL-4-NITROANILIDE(7300-59-6)
• EPA Substance Registry System: GAMMA-L-GLUTAMYL-4-NITROANILIDE(7300-59-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 7300-59-6(Hazardous Substances Data)

Usage

Chemical Properties

cream coloured to light yellow powder

Uses

Substrate for gamma-glutamyl transpeptidase

InChI:InChI=1/C11H13N3O5/c12-10(15)6-5-9(11(16)17)13-7-1-3-8(4-2-7)14(18)19/h1-4,9,13H,5-6H2,(H2,12,15)(H,16,17)/t9-/m0/s1

Synthetic route

(S)-2-Benzyloxycarbonylamino-4-(4-nitro-phenylcarbamoyl)-butyric acid (113277-32-0) → L-glutamic acid 5-(4-nitroanilide) (7300-59-6)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol

(S)-4-[2-(4-Nitro-phenylcarbamoyl)-ethyl]-5-oxo-oxazolidine-3-carboxylic acid benzyl ester (848215-13-4) → L-glutamic acid 5-(4-nitroanilide) (7300-59-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium hydroxide / tetrahydrofuran; H2O / 0.5 h / 5 °C 2: hydrogen / Pd/C / methanol View Scheme

L-glutamic acid (56-86-0) → L-glutamic acid 5-(4-nitroanilide) (7300-59-6)

Conditions	Yield
Multi-step reaction with 6 steps 1: 98 percent / triethylamine / methanol / 3 h 2: 90 percent / toluenesulfonic acid / toluene / 3 h / Heating 3: thionyl chloride / CH2Cl2 / 0.5 h / Heating 4: pyridine / CH2Cl2 / 0.25 h / 20 °C 5: lithium hydroxide / tetrahydrofuran; H2O / 0.5 h / 5 °C 6: hydrogen / Pd/C / methanol View Scheme

N-benzyloxycarbonyl-L-glutamic acid (1155-62-0) → L-glutamic acid 5-(4-nitroanilide) (7300-59-6)

Conditions	Yield
Multi-step reaction with 5 steps 1: 90 percent / toluenesulfonic acid / toluene / 3 h / Heating 2: thionyl chloride / CH2Cl2 / 0.5 h / Heating 3: pyridine / CH2Cl2 / 0.25 h / 20 °C 4: lithium hydroxide / tetrahydrofuran; H2O / 0.5 h / 5 °C 5: hydrogen / Pd/C / methanol View Scheme

(S)-4-<2'-(Chloroformyl)ethyl>-5-oxooxazolidin-3-carbonsaeure-benzylester (58456-26-1) → L-glutamic acid 5-(4-nitroanilide) (7300-59-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine / CH2Cl2 / 0.25 h / 20 °C 2: lithium hydroxide / tetrahydrofuran; H2O / 0.5 h / 5 °C 3: hydrogen / Pd/C / methanol View Scheme

(S)-3-[3-(benzyloxycarbonyl)-5-oxooxazolidin-4-yl]propanoic acid (23632-67-9) → L-glutamic acid 5-(4-nitroanilide) (7300-59-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: thionyl chloride / CH2Cl2 / 0.5 h / Heating 2: pyridine / CH2Cl2 / 0.25 h / 20 °C 3: lithium hydroxide / tetrahydrofuran; H2O / 0.5 h / 5 °C 4: hydrogen / Pd/C / methanol View Scheme

N-tert-butoxycarbonyl glutamic acid tert-butyl ester (24277-39-2) + 4-nitro-aniline (100-01-6) → L-glutamic acid 5-(4-nitroanilide) (7300-59-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h / 120 °C / Microwave irradiation 2: hydrogenchloride / 1,4-dioxane / 4 h / 40 °C View Scheme

C20H29N3O7 → L-glutamic acid 5-(4-nitroanilide) (7300-59-6)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 40℃; for 4h;

L-glutamic acid 5-(4-nitroanilide) (7300-59-6) → 4-nitro-aniline (100-01-6)

Conditions	Yield
at 37℃; 0.1 M Tris-HCl buffer, γ-glutamyltransferase from mushroom Lentinus edodes; other enzyme; Michaelis constant Km and Vmax determination;
With religiosin B at 37℃; pH=8; Kinetics; aq. buffer; Enzymatic reaction;
With religiosin C at 37℃; pH=8; Kinetics; Concentration; aq. buffer; Enzymatic reaction;

glycylglycine (556-50-3) + L-glutamic acid 5-(4-nitroanilide) (7300-59-6) → L-α-glutamyl=>glycyl=>glycine (6706-20-3)

Conditions	Yield
With HCl buffer; rat kidney γ-glutamyltranspeptidase pH=8.0; Enzyme kinetics;

L-glutamic acid 5-(4-nitroanilide) (7300-59-6) + D-glutamic acid γ-p-nitroanilide (60133-17-7) → (S)-2-((R)-2-Amino-4-carboxy-butyrylamino)-4-(4-nitro-phenylcarbamoyl)-butyric acid

Conditions	Yield
With HCl buffer; rat kidney γ-glutamyltranspeptidase pH=8.0; Enzyme kinetics;

L-glutamic acid 5-(4-nitroanilide) (7300-59-6) → L-glutamic acid (56-86-0) + 4-nitro-aniline (100-01-6)

Conditions	Yield
With marine bivalve lysozyme; MOPS buffer; Tapes japonica at 37℃; pH=7.0; Enzyme kinetics;
With recombinant Pseudomonas nitroreducens IFO12694 γ-glutamyltranspeptidase at 30℃; for 0.0333333h; pH=10.5; aq. buffer; Enzymatic reaction;
With C-terminal hexahistidine-tagged Geobacillus thermodenitrificans NG80-2 γ-glutamyl transpeptidase at 52℃; pH=8; Kinetics; aq. Tris-HCl buffer; Enzymatic reaction;

glycylglycine (556-50-3) + L-glutamic acid 5-(4-nitroanilide) (7300-59-6) → 4-nitro-aniline (100-01-6)

Conditions	Yield
With Tris-HCl buffer at 37℃; pH=8.0; Enzyme kinetics; Further Variations:; Catalysts;

glycylglycine (556-50-3) + L-glutamic acid 5-(4-nitroanilide) (7300-59-6) → gamma-Glutamyl-glycyl-glycine (13640-39-6) + 4-nitro-aniline (100-01-6)

Conditions	Yield
With γ-glutamyltransferase from Bacillus subtilis In aq. phosphate buffer at 22℃; pH=8.5; pH-value; Enzymatic reaction;

Upstream product

• 113277-32-0 (S)-2-Benzyloxycarbonylamino-4-(4-nitro-phenylcarbamoyl)-butyric acid 
• 848215-13-4 (S)-4-[2-(4-Nitro-phenylcarbamoyl)-ethyl]-5-oxo-oxazolidine-3-carboxylic acid benzyl ester 
• 56-86-0 L-glutamic acid 
• 1155-62-0 N-benzyloxycarbonyl-L-glutamic acid 
• 58456-26-1 (S)-4-<2'-(Chloroformyl)ethyl>-5-oxooxazolidin-3-carbonsaeure-benzylester 
• 23632-67-9 (S)-3-[3-(benzyloxycarbonyl)-5-oxooxazolidin-4-yl]propanoic acid 
• 24277-39-2 N-tert-butoxycarbonyl glutamic acid tert-butyl ester 
• 100-01-6 4-nitro-aniline 

Downstream Products

• 100-01-6 4-nitro-aniline 
• 56-86-0 L-glutamic acid 
• 13640-39-6 gamma-Glutamyl-glycyl-glycine 

Relevant articles and documents

2-Substituted Nγ-glutamylanilides as novel probes of ASCT2 with improved potency

Herein, we report the discovery and structure-activity relationships (SAR) of 2-substituted glutamylanilides as novel probes of the steric environment comprising the amino acid binding domain of alanine-serine-cysteine transporter subtype 2 (ASCT2). Focused library development led to three novel, highly potent ASCT2 inhibitors, with N-(2-(morpholinomethyl)phenyl)-l-glutamine exhibiting the greatest potency in a live-cell glutamine uptake assay. This level of potency represents a three-fold improvement over the most potent, previously reported inhibitor in this series, GPNA. Furthermore, this and other compounds in the series exhibit tractable chemical properties for further development as potential therapeutic leads.

ISOLATION OF GAMMA-GLUTAMYL TRANSPEPTIDASE FROM HOG KIDNEY.

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