Product Name

  • Name

    GAMMA-L-GLUTAMYL-4-NITROANILIDE

  • EINECS 230-748-5
  • CAS No. 7300-59-6
  • Article Data4
  • CAS DataBase
  • Density 1.463 g/cm3
  • Solubility
  • Melting Point 185-188°C
  • Formula C11H13N3O5
  • Boiling Point 590.6 °C at 760 mmHg
  • Molecular Weight 267.241
  • Flash Point 311 °C
  • Transport Information
  • Appearance cream coloured to light yellow powder
  • Safety 22-24/25
  • Risk Codes
  • Molecular Structure Molecular Structure of 7300-59-6 (GAMMA-L-GLUTAMYL-4-NITROANILIDE)
  • Hazard Symbols
  • Synonyms Glutaranilicacid, 2-amino-4'-nitro-, L- (8CI);L-Glutamic acid g-p-nitroanilide;L-Glutamyl-4-nitroanilide;L-g-Glutamyl-p-nitroanilide;g-Glutamyl-p-nitroanilide;g-L-Glu-p-nitroanilide;g-L-Glutamyl-p-nitroanilide;
  • PSA 138.24000
  • LogP 2.02190

Synthetic route

(S)-2-Benzyloxycarbonylamino-4-(4-nitro-phenylcarbamoyl)-butyric acid
113277-32-0

(S)-2-Benzyloxycarbonylamino-4-(4-nitro-phenylcarbamoyl)-butyric acid

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

L-glutamic acid 5-(4-nitroanilide)

Conditions
ConditionsYield
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

(S)-4-[2-(4-Nitro-phenylcarbamoyl)-ethyl]-5-oxo-oxazolidine-3-carboxylic acid benzyl ester

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

L-glutamic acid 5-(4-nitroanilide)

Conditions
ConditionsYield
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

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

L-glutamic acid 5-(4-nitroanilide)

Conditions
ConditionsYield
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

N-benzyloxycarbonyl-L-glutamic acid

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

L-glutamic acid 5-(4-nitroanilide)

Conditions
ConditionsYield
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

(S)-4-<2'-(Chloroformyl)ethyl>-5-oxooxazolidin-3-carbonsaeure-benzylester

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

L-glutamic acid 5-(4-nitroanilide)

Conditions
ConditionsYield
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

(S)-3-[3-(benzyloxycarbonyl)-5-oxooxazolidin-4-yl]propanoic acid

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

L-glutamic acid 5-(4-nitroanilide)

Conditions
ConditionsYield
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

N-tert-butoxycarbonyl glutamic acid tert-butyl ester

4-nitro-aniline
100-01-6

4-nitro-aniline

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

L-glutamic acid 5-(4-nitroanilide)

Conditions
ConditionsYield
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

C20H29N3O7

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

L-glutamic acid 5-(4-nitroanilide)

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane at 40℃; for 4h;
L-glutamic acid 5-(4-nitroanilide)
7300-59-6

L-glutamic acid 5-(4-nitroanilide)

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
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

glycylglycine

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

L-glutamic acid 5-(4-nitroanilide)

L-α-glutamyl=>glycyl=>glycine
6706-20-3

L-α-glutamyl=>glycyl=>glycine

Conditions
ConditionsYield
With HCl buffer; rat kidney γ-glutamyltranspeptidase pH=8.0; Enzyme kinetics;
L-glutamic acid 5-(4-nitroanilide)
7300-59-6

L-glutamic acid 5-(4-nitroanilide)

D-glutamic acid γ-p-nitroanilide
60133-17-7

D-glutamic acid γ-p-nitroanilide

(S)-2-((R)-2-Amino-4-carboxy-butyrylamino)-4-(4-nitro-phenylcarbamoyl)-butyric acid

(S)-2-((R)-2-Amino-4-carboxy-butyrylamino)-4-(4-nitro-phenylcarbamoyl)-butyric acid

Conditions
ConditionsYield
With HCl buffer; rat kidney γ-glutamyltranspeptidase pH=8.0; Enzyme kinetics;
L-glutamic acid 5-(4-nitroanilide)
7300-59-6

L-glutamic acid 5-(4-nitroanilide)

A

L-glutamic acid
56-86-0

L-glutamic acid

B

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
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

glycylglycine

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

L-glutamic acid 5-(4-nitroanilide)

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
With Tris-HCl buffer at 37℃; pH=8.0; Enzyme kinetics; Further Variations:; Catalysts;
glycylglycine
556-50-3

glycylglycine

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

L-glutamic acid 5-(4-nitroanilide)

A

gamma-Glutamyl-glycyl-glycine
13640-39-6

gamma-Glutamyl-glycyl-glycine

B

4-nitro-aniline
100-01-6

4-nitro-aniline

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

L-Glutamyl-4-nitroanilide Specification

The L-Glutamine,N-(4-nitrophenyl)-, with the CAS registry number 7300-59-6, is also known as (S)-2-Amino-5-((4-nitrophenyl)amino)-5-oxopentanoic acid. Its EINECS number is 230-748-5. This chemical's molecular formula is C11H13N3O5 and molecular weight is 267.24. What's more, its systematic name is N-(4-nitrophenyl)-L-glutamine. It should be sealed and stored in a cool and dry place at the temperature of 2-8 °C.

Physical properties of L-Glutamine,N-(4-nitrophenyl)- are: (1)ACD/LogP: 1.29; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.21; (4)ACD/LogD (pH 7.4): -1.22; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 8; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 95.67 Å2; (13)Index of Refraction: 1.643; (14)Molar Refractivity: 66.02 cm3; (15)Molar Volume: 182.5 cm3; (16)Polarizability: 26.17×10-24 cm3; (17)Surface Tension: 73.2 dyne/cm; (18)Density: 1.463 g/cm3; (19)Flash Point: 311 °C; (20)Enthalpy of Vaporization: 92.67 kJ/mol; (21)Boiling Point: 590.6 °C at 760 mmHg; (22)Vapour Pressure: 8.57E-15 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
You should not breathe dust, and you also should avoid contact with skin.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: O=C(Nc1ccc(cc1)[N+]([O-])=O)CC[C@@H](C(=O)O)N
(2)InChI: InChI=1/C11H13N3O5/c12-9(11(16)17)5-6-10(15)13-7-1-3-8(4-2-7)14(18)19/h1-4,9H,5-6,12H2,(H,13,15)(H,16,17)/t9-/m0/s1
(3)InChIKey: WMZTYIRRBCGARG-VIFPVBQEBD

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