N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine
L-glutamine
Conditions | Yield |
---|---|
With sodium azide In N,N-dimethyl-formamide at 50℃; for 24h; | 97% |
A
L-glutamine
Conditions | Yield |
---|---|
With hydrogenchloride; water In methanol at 30℃; for 2h; | A n/a B 95% |
With hydrogenchloride In methanol; water at 30℃; for 2h; | A 0.05 g B 95% |
L-glutamine
Conditions | Yield |
---|---|
With hydrogenchloride In methanol at 70℃; for 20h; | 92% |
L-glutamine
Conditions | Yield |
---|---|
With hydrogenchloride In methanol at 70℃; for 20h; | 85% |
Conditions | Yield |
---|---|
With phosphoenolpyruvic acid; Imidazole-HCl buffer; ammonium chloride; adenosine 5'-diphosphate; magnesium chloride at 37℃; for 6h; pyruvate kinase, glutamine synthetase; | 79% |
With ammonia unter der Einwirkung von Enzym-Praeparaten aus verschiedenen tierischen Geweben; | |
With ammonia unter der Einwirkung von Streptococcus-Arten in Gegenwart von d-Glucose; |
L-glutamine
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran; water at 20℃; for 5h; | 79% |
L-glutamine
Conditions | Yield |
---|---|
With ruthenium nanoparticles dispersed in a polyvinylpyrrolidone matrix; amberlyst A-21 In methanol; dichloromethane | 59% |
Conditions | Yield |
---|---|
With ethanol; nickel |
N-trityl-L-glutamic acid 5-methyl ester
L-glutamine
Conditions | Yield |
---|---|
With ammonia Erwaermen des Reaktionsprodukts mit wss.Essigsaeure; |
5-amino-2(S)-{[(4-methylphenyl)sulfonyl]amino}-5-oxopentanoic acid
L-glutamine
Conditions | Yield |
---|---|
With hydrogen bromide; acetic acid; phenol |
(S)-4-Carbamoyl-2-[2-(4-methoxy-phenyl)-2-oxo-ethoxycarbonylamino]-butyric acid
A
L-glutamine
B
1-(4-methoxyphenyl)ethanone
Conditions | Yield |
---|---|
Irradiation; mild conditions; |
Conditions | Yield |
---|---|
With ammonium chloride In water at 30℃; for 0.166667h; γ-glutamylmethylamide synthetase from Methylophaga sp. AA-30, 0.5 M Tris HCl buffer pH 7.5, 2.5 M 2-mercaptoethanol, 0.1 M MnCl2, 0.1 M ATP; relative enzyme activity compared to methylamine, Km; |
Puwainaphycin E
A
L-valine
B
L-glutamine
C
(2R,3R,4S)-3-Amino-2-hydroxy-4-methyl-hexadecanoic acid
D
L-proline
Conditions | Yield |
---|---|
With hydrogenchloride at 100℃; for 24h; Further byproducts given; |
Conditions | Yield |
---|---|
With hydrogenchloride at 100℃; for 24h; Further byproducts given; |
Nα,Nca-di-tert-butyloxycarbonylglutamine
L-glutamine
Conditions | Yield |
---|---|
With hydrogen bromide In acetic acid |
L-glutamine
Conditions | Yield |
---|---|
With hydrogenchloride; water In acetic acid at 55℃; for 0.833333h; |
Conditions | Yield |
---|---|
With Tris-HCl buffer; N74D Escherichia coli asparagine synthetase B mutant; BIS-TRIS; magnesium chloride at 37℃; for 0.333333h; pH=6.5; Enzyme kinetics; Further Variations:; Reagents; pH-values; Hydrolysis; |
L-glutamine
Conditions | Yield |
---|---|
With sodium carbonate; hydrazine |
L-glutamine
Conditions | Yield |
---|---|
With methanol; palladium; acetic acid Hydrogenolyse; |
L-glutamine
Conditions | Yield |
---|---|
With palladium; acetic acid Hydrogenolyse; | |
With palladium; acetic acid Hydrogenolyse; | |
With phosphonium iodide; acetic acid at 40 - 50℃; | |
With palladium; acetic acid Hydrogenolyse; | |
With palladium; acetic acid Hydrogenolyse; |
N2-benzyloxycarbonyl-L-glutamine methyl ester
A
glutamine
B
L-glutamine
Conditions | Yield |
---|---|
Ansaeuern mit wss. HCl und Hydrieren des Reaktionsgemisches an Palladium; |
(S)-methyl 5-amino-4-{[(benzyloxy)carbonyl]amino}-5-oxopentanoate
A
glutamine
B
L-glutamine
Conditions | Yield |
---|---|
Ansaeuern mit wss. HCl und Hydrieren des Reaktionsgemisches an Palladium; |
Conditions | Yield |
---|---|
With acylase I from pig kidney; water In glycerol at 37℃; for 3h; pH=7.5; Equilibrium constant; |
Conditions | Yield |
---|---|
With (2R,3R,11R,12R)-(+)-18-crown-6-2,3,11,12-tetracarbonic acid | |
With R-(3,3'-dibromo-1,1'-binaphthyl)-20-crown-6 coated C18 silica gel column at 25℃; pH=2; Resolution of racemate; |
Conditions | Yield |
---|---|
With sodium phosphate buffer; leucine amino peptidase at 37℃; pH=7.2; Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With sodium phosphate buffer; leucine amino peptidase at 37℃; pH=7.2; Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With Pseudomonas taetrolens Y-30 glutamine synthetase EC 6.3.1.2; ammonium chloride; magnesium chloride; imidazole buffer at 30℃; pH=8.0; Enzyme kinetics; Further Variations:; pH-values; Reagents; |
Boc-Glu-OBn
L-glutamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 2: 1 N HCl, H2O / acetic acid / 0.83 h / 55 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: triethylamine; CHCl3 2: methanol. sodium methylate 3: palladium; triethylamine; cyclohexane / Hydrogenation 4: methanol.NH3 / Erwaermen des Reaktionsprodukts mit wss.Essigsaeure View Scheme |
L-glutamine
methyl 1-β-D-ribofuranosyl-1,2,4-triazole-3-carboximidate
1-β-D-ribofuranosyl-1,2,4-triazole-3-N-(α-carboxy-4'-butyramido)carboxamidine
Conditions | Yield |
---|---|
In methanol for 168h; Ambient temperature; | 100% |
L-glutamine
1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate
Conditions | Yield |
---|---|
In water pH=4.95; Cooling with ice; | 100% |
L-glutamine
Conditions | Yield |
---|---|
In water at 10℃; pH=Ca. 2.3 - 2.5; | 100% |
L-glutamine
Conditions | Yield |
---|---|
In water at 10℃; pH=Ca. 2.8; | 100% |
Conditions | Yield |
---|---|
In water pH=2.1 - 5.06; Inert atmosphere; Cooling with ice; | 100% |
Conditions | Yield |
---|---|
In water for 0.0666667h; Irradiation; | 99% |
With sodium hydroxide |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In 1,4-dioxane; water for 48h; Ambient temperature; | 99% |
Conditions | Yield |
---|---|
With sodium hydroxide In water aq. soln. of K2PdCl6 and amino-acid was stirred and to the mixt. was dropped 1 N NaOH within 20 min, stirring was continued for 18 h; soln. was filtered, residue was washed with water, then ethanol and ether and dried in vac. over P2O5; elem. anal.; | 99% |
L-glutamine
α-carbobenzoxy-L-tryptophan p-nitrophenyl ester
N-benzyloxycarbonyl-L-tryptophan-L-glutamine
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran; water at 20℃; | 99% |
Conditions | Yield |
---|---|
With sodium carbonate In 1,4-dioxane; water at 0 - 20℃; Inert atmosphere; | 98% |
With sodium hydroxide In water; toluene at 25 - 30℃; pH=11 - 12; | 88.5% |
Stage #1: L-glutamine; benzyl chloroformate With sodium hydrogencarbonate In water; toluene at 20℃; Inert atmosphere; Stage #2: With hydrogenchloride In water | 86% |
L-glutamine
N-Benzyloxycarbonyl-N-trifluoromethylsulfonyl-4-trifluoromethylanilide
Cbz-L-Gln
Conditions | Yield |
---|---|
With water; triethylamine In 1,4-dioxane at 20℃; for 1h; Acylation; | 98% |
L-glutamine
(R)-N-(2-benzoyl-4-chlorophenyl)-1-[(3,4-dichlorophenyl)methyl]-2-pyrrolidinecarboxamide
nickel(II) acetate tetrahydrate
Conditions | Yield |
---|---|
With potassium carbonate In methanol at 60℃; for 3h; Temperature; | 98% |
L-glutamine
9-methoxy-9-BBN
Conditions | Yield |
---|---|
In methanol; hexane for 1h; Reflux; | 98% |
Conditions | Yield |
---|---|
With lithium hydroxide In ethanol refluxing (1.5 h), Mn-salt addn., refluxing (1.5 h); filtering (room temp.), drying (25°C); elem. anal.; | 95.3% |
Conditions | Yield |
---|---|
95% | |
Stage #1: L-glutamine With sodium hydroxide In 1,4-dioxane; water Large scale; Stage #2: di-tert-butyl dicarbonate In 1,4-dioxane at 0 - 20℃; for 4h; Reagent/catalyst; Solvent; Temperature; Large scale; | 90.7% |
With sodium hydroxide In 1,4-dioxane for 1h; | 90% |
L-glutamine
cholin hydroxide
2-hydroxyethyltrimethylammonium L-glutaminate
Conditions | Yield |
---|---|
In water at 3℃; for 48h; Darkness; | 95% |
L-glutamine
phenyl isothiocyanate
3-(5-oxo-1-phenyl-2-thioxoimidazolidin-4-yl)propanamide
Conditions | Yield |
---|---|
With triethylamine In water; N,N-dimethyl-formamide at 20℃; for 3h; | 95% |
L-glutamine
2,2-bis(4'-nitrophenyl)ethyl-N-succinimidyl carbonate
Nα-<2,2-bis(4'-nitrophenyl)ethoxycarbonyl>-glutamine
Conditions | Yield |
---|---|
With triethylamine In 1,4-dioxane; water Ambient temperature; | 94% |
Conditions | Yield |
---|---|
With sodium hydroxide In 1,4-dioxane at 0 - 20℃; for 123h; | 93% |
L-glutamine
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine
Conditions | Yield |
---|---|
With sodium carbonate In 1,4-dioxane; water at 0 - 20℃; | 93% |
With sodium carbonate In tetrahydrofuran; water | 84% |
Stage #1: L-glutamine With N-cyclohexyl-cyclohexanamine In acetone at 20℃; Stage #2: N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide With sodium carbonate In water; acetonitrile at 0 - 20℃; pH=8; Stage #3: With potassium hydrogensulfate In water; acetonitrile pH=2 - 3; | 54% |
L-glutamine
p-toluenesulfonyl chloride
5-amino-2(S)-{[(4-methylphenyl)sulfonyl]amino}-5-oxopentanoic acid
Conditions | Yield |
---|---|
With magnesium oxide In water at 5℃; | 92% |
With sodium hydroxide In 1,4-dioxane for 2.5h; | 73% |
With sodium hydroxide In water at 80 - 90℃; | 58% |
L-glutamine
tetraethylammonium hydroxide
tetraethylammonium L-glutaminate
Conditions | Yield |
---|---|
In water at 20℃; for 2h; | 91% |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In water at 20℃; for 0.5h; pH=8.5; | 90.8% |
Conditions | Yield |
---|---|
In isopropyl alcohol for 2h; Heating; | 90% |
Conditions | Yield |
---|---|
In pyridine; water for 2h; Ambient temperature; | A n/a B 90% |
L-glutamine
benzyl (4-(chlorocarbonyl)phenyl)(methyl)carbamate
N2-<4-<<(benzyloxy)carbonyl>methylamino>benzoyl>-L-glutamine
Conditions | Yield |
---|---|
With sodium hydroxide In 1,4-dioxane at 0 - 5℃; | 90% |
L-glutamine
ethylamine
N-ethyl-L-glutamine
Conditions | Yield |
---|---|
With recombinant Bacillus subtilis γ-glutamyltranspeptidase In water at 37℃; for 5h; pH=10; Concentration; pH-value; Temperature; Enzymatic reaction; | 90% |
With glutaminase from Pseudomonas nitroreducens IFO 12694; imidazole buffer In water at 30℃; relative rate of glutamyl transfer; | |
biosynthesis by immobilized cells of Pseudomonas nitroreducens; | |
With recombinant Pseudomonas nitroreducens IFO12694 γ-glutamyltranspeptidase at 30℃; for 0.333333h; pH=10.5; aq. buffer; Enzymatic reaction; | |
With glutaminase immobilised on SBA-15 type mesoporous silica at 20℃; for 1h; Reagent/catalyst; pH-value; Temperature; Flow reactor; Enzymatic reaction; |
L-Glutamine (CAS NO.77668-42-9) is reported in EPA TSCA Inventory.
L-Glutamine, with the IUPAC Name of (2S)-2,5-Diamino-5-oxopentanoic acid, is one kind of white crystalline powder. And its Classification Code are including Dietary supplement; Drug / Therapeutic Agent; Human Data; Mutation data. L-Glutamine(CAS NO.56-85-9) is the most abundant amino acid (building block of protein) in the body. The popular amino acid L-Glutamine is found in protein powders, beans, meats, fish, poultry, dairy products, and of course. It is used in the gut and immune system to maintain optimal performance. 60% of free-form amino acids floating in skeletal muscles is L-Glutamine.
Physical properties about L-Glutamine are: (1)ACD/LogP: -1.576; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -4.08; (4)ACD/LogD (pH 7.4): -4.08; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 5; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 5; (12)Index of Refraction: 1.524; (13)Molar Refractivity: 33.837 cm3; (14)Molar Volume: 110.546 cm3; (15)Polarizability: 13.414 10-24cm3; (16)Surface Tension: 64.588996887207 dyne/cm; (17)Density: 1.322 g/cm3; (18)Flash Point: 223.272 °C; (19)Enthalpy of Vaporization: 77.128 kJ/mol; (20)Boiling Point: 445.568 °C at 760 mmHg
Uses of L-Glutamine:
1). L-Glutamine (CAS NO.77668-42-9) has been studied extensively over the past 10–15 years and has been shown to be useful in treatment of serious illnesses, injury, trauma, burns, cancer and its treatment related side-effects as well as in wound healing for postoperative patients.
2). Glutamine is also marketed as a supplement used for muscle growth in weightlifting, bodybuilding, endurance, and other sports.
3). Glutamine has also been taken to enhance brain function as it fuels two of the brain's most important neurotransmitters.
4). It has also been used in the treatment of ADHD, anxiety,and depression.
5). It has also been used in recovery programs to break sugar craving cycles in alcoholics and assist diabetics in the management of sugar cravings.
6). It is also used as an anti-inflammatory in the treatment of autoimmune diseases and preserves Glutathione levels in the liver.
You can still convert the following datas into molecular structure:
(1)InChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)/t3-/m0/s1;
(2)InChIKey=ZDXPYRJPNDTMRX-VKHMYHEASA-N;
(3)SmilesC([C@@H](C(=O)O)N)CC(N)=O
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
man | TDLo | oral | 27mg/kg/1W-I (27mg/kg) | BEHAVIORAL: EUPHORIA | American Journal of Psychiatry. Vol. 141, Pg. 1302, 1984. |
mouse | LD50 | oral | 21700mg/kg (21700mg/kg) | Drugs in Japan Vol. 6, Pg. 228, 1982. | |
rat | LD50 | oral | 7500mg/kg (7500mg/kg) | Drugs in Japan Vol. 6, Pg. 228, 1982. |
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