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56-85-9 Usage

General Description

L-Glutamine is an amino acid and a key building block of proteins in the body. It is classified as a conditionally essential amino acid, as the body can typically synthesize enough of it under normal conditions, but may need additional supplementation during times of illness, stress, or intense physical activity. L-Glutamine plays a crucial role in various physiological functions, including supporting immune system function, maintaining the integrity of the intestinal lining, and facilitating the removal of ammonia from the body. It is also utilized as a source of energy for cells, particularly in the gut and immune system. Additionally, L-Glutamine has been studied for its potential benefits in supporting muscle recovery and reducing muscle soreness after exercise. As a result, it is commonly used as a supplement by athletes and individuals looking to support their overall health and wellness.

Check Digit Verification of cas no

The CAS Registry Mumber 56-85-9 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 6 respectively; the second part has 2 digits, 8 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 56-85:
(4*5)+(3*6)+(2*8)+(1*5)=59
59 % 10 = 9
So 56-85-9 is a valid CAS Registry Number.
InChI:InChI=1/2C5H10N2O3/c2*6-3(5(9)10)1-2-4(7)8/h2*3H,1-2,6H2,(H2,7,8)(H,9,10)

56-85-9 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (G0063)  L-Glutamine  >99.0%(T)

  • 56-85-9

  • 25g

  • 180.00CNY

  • Detail
  • TCI America

  • (G0063)  L-Glutamine  >99.0%(T)

  • 56-85-9

  • 100g

  • 470.00CNY

  • Detail
  • TCI America

  • (G0063)  L-Glutamine  >99.0%(T)

  • 56-85-9

  • 500g

  • 1,450.00CNY

  • Detail
  • Alfa Aesar

  • (A14201)  L-Glutamine, 99%   

  • 56-85-9

  • 50g

  • 265.0CNY

  • Detail
  • Alfa Aesar

  • (A14201)  L-Glutamine, 99%   

  • 56-85-9

  • 250g

  • 1091.0CNY

  • Detail
  • Alfa Aesar

  • (A14201)  L-Glutamine, 99%   

  • 56-85-9

  • 1000g

  • 3771.0CNY

  • Detail
  • Sigma

  • (G7513)  L-Glutaminesolution  200 mM, solution, sterile-filtered, BioXtra, suitable for cell culture

  • 56-85-9

  • G7513-20ML

  • 101.79CNY

  • Detail
  • Sigma

  • (G7513)  L-Glutaminesolution  200 mM, solution, sterile-filtered, BioXtra, suitable for cell culture

  • 56-85-9

  • G7513-100ML

  • 401.31CNY

  • Detail
  • Sigma-Aldrich

  • (76523)  L-Glutamine  certified reference material, TraceCERT®

  • 56-85-9

  • 76523-100MG

  • 1,117.35CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1125)  L-Glutamine  pharmaceutical secondary standard; traceable to USP

  • 56-85-9

  • PHR1125-1G

  • 732.19CNY

  • Detail
  • Sigma

  • (G3126)  L-Glutamine  ReagentPlus®, ≥99% (HPLC)

  • 56-85-9

  • G3126-100G

  • 742.95CNY

  • Detail
  • Sigma

  • (G3126)  L-Glutamine  ReagentPlus®, ≥99% (HPLC)

  • 56-85-9

  • G3126-250G

  • 1,401.66CNY

  • Detail

56-85-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name L-glutamine

1.2 Other means of identification

Product number -
Other names L-(+)-Glutamine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:56-85-9 SDS

56-85-9Synthetic route

N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine
71989-20-3

N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine

L-glutamine
56-85-9

L-glutamine

Conditions
ConditionsYield
With sodium azide In N,N-dimethyl-formamide at 50℃; for 24h;97%
C42H33ClN4NiO4

C42H33ClN4NiO4

A

L-glutamine
56-85-9

L-glutamine

(R)-N-(2-benzoyl-4-chlorophenyl)-2-[3,5-dihydro-4H-dinaphtho[2,1-c:1',2'-e]azepine-4-yl]acetamide

(R)-N-(2-benzoyl-4-chlorophenyl)-2-[3,5-dihydro-4H-dinaphtho[2,1-c:1',2'-e]azepine-4-yl]acetamide

Conditions
ConditionsYield
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%
4-carbamoyl-2-[(E,Z)-4,4,4-trifluoro-3-oxo-1-butenylamino]butanoic acid

4-carbamoyl-2-[(E,Z)-4,4,4-trifluoro-3-oxo-1-butenylamino]butanoic acid

L-glutamine
56-85-9

L-glutamine

Conditions
ConditionsYield
With hydrogenchloride In methanol at 70℃; for 20h;92%
4-carbamoyl-2-[(E,Z)-4,4,4-trichloro-3-oxo-1-butenylamino]butanoic acid

4-carbamoyl-2-[(E,Z)-4,4,4-trichloro-3-oxo-1-butenylamino]butanoic acid

L-glutamine
56-85-9

L-glutamine

Conditions
ConditionsYield
With hydrogenchloride In methanol at 70℃; for 20h;85%
L-glutamic acid
56-86-0

L-glutamic acid

L-glutamine
56-85-9

L-glutamine

Conditions
ConditionsYield
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;
(S)-3-(5'-oxo-9λ4-boraspiro[bicyclo[3.3.1]nonane-9,2'-[1,3,2]oxazaborolidin]-4'-yl)propanamide

(S)-3-(5'-oxo-9λ4-boraspiro[bicyclo[3.3.1]nonane-9,2'-[1,3,2]oxazaborolidin]-4'-yl)propanamide

L-glutamine
56-85-9

L-glutamine

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran; water at 20℃; for 5h;79%
C5H10N2O3*H3N*ClH

C5H10N2O3*H3N*ClH

L-glutamine
56-85-9

L-glutamine

Conditions
ConditionsYield
With ruthenium nanoparticles dispersed in a polyvinylpyrrolidone matrix; amberlyst A-21 In methanol; dichloromethane59%
glutamic acid γ-hydrazide
1820-73-1

glutamic acid γ-hydrazide

L-glutamine
56-85-9

L-glutamine

Conditions
ConditionsYield
With ethanol; nickel
N-trityl-L-glutamic acid 5-methyl ester
55878-80-3

N-trityl-L-glutamic acid 5-methyl ester

L-glutamine
56-85-9

L-glutamine

Conditions
ConditionsYield
With ammonia Erwaermen des Reaktionsprodukts mit wss.Essigsaeure;
5-amino-2(S)-{[(4-methylphenyl)sulfonyl]amino}-5-oxopentanoic acid
42749-49-5

5-amino-2(S)-{[(4-methylphenyl)sulfonyl]amino}-5-oxopentanoic acid

L-glutamine
56-85-9

L-glutamine

Conditions
ConditionsYield
With hydrogen bromide; acetic acid; phenol
(S)-4-Carbamoyl-2-[2-(4-methoxy-phenyl)-2-oxo-ethoxycarbonylamino]-butyric acid
125219-08-1

(S)-4-Carbamoyl-2-[2-(4-methoxy-phenyl)-2-oxo-ethoxycarbonylamino]-butyric acid

A

L-glutamine
56-85-9

L-glutamine

B

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
Irradiation; mild conditions;
monosodium glutamate
142-47-2

monosodium glutamate

L-glutamine
56-85-9

L-glutamine

Conditions
ConditionsYield
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
142998-32-1

Puwainaphycin E

A

L-valine
72-18-4

L-valine

B

L-glutamine
56-85-9

L-glutamine

C

(2R,3R,4S)-3-Amino-2-hydroxy-4-methyl-hexadecanoic acid
138754-66-2

(2R,3R,4S)-3-Amino-2-hydroxy-4-methyl-hexadecanoic acid

D

L-proline
147-85-3

L-proline

Conditions
ConditionsYield
With hydrogenchloride at 100℃; for 24h; Further byproducts given;
Puwainaphycin B
142998-31-0

Puwainaphycin B

A

L-valine
72-18-4

L-valine

B

L-glutamine
56-85-9

L-glutamine

C

(2R,3R,4S)-3-Amino-2-hydroxy-4-methyl-14-oxo-octadecanoic acid

(2R,3R,4S)-3-Amino-2-hydroxy-4-methyl-14-oxo-octadecanoic acid

D

L-proline
147-85-3

L-proline

Conditions
ConditionsYield
With hydrogenchloride at 100℃; for 24h; Further byproducts given;
Nα,Nca-di-tert-butyloxycarbonylglutamine
98115-14-1

Nα,Nca-di-tert-butyloxycarbonylglutamine

L-glutamine
56-85-9

L-glutamine

Conditions
ConditionsYield
With hydrogen bromide In acetic acid
Boc-L-Glu-γ-DHA-CONHCH3

Boc-L-Glu-γ-DHA-CONHCH3

L-glutamine
56-85-9

L-glutamine

Conditions
ConditionsYield
With hydrogenchloride; water In acetic acid at 55℃; for 0.833333h;
(S)-2-amino-4-cyano-butyric acid
6232-22-0

(S)-2-amino-4-cyano-butyric acid

L-glutamine
56-85-9

L-glutamine

Conditions
ConditionsYield
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;
-5-amide

-5-amide

L-glutamine
56-85-9

L-glutamine

Conditions
ConditionsYield
With sodium carbonate; hydrazine
-1-benzyl ester-5-amide

-1-benzyl ester-5-amide

L-glutamine
56-85-9

L-glutamine

Conditions
ConditionsYield
With methanol; palladium; acetic acid Hydrogenolyse;
-5-amide

-5-amide

L-glutamine
56-85-9

L-glutamine

Conditions
ConditionsYield
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
13907-82-9, 2650-67-1

N2-benzyloxycarbonyl-L-glutamine methyl ester

aqueous NaOH

aqueous NaOH

A

glutamine
636-65-7

glutamine

B

L-glutamine
56-85-9

L-glutamine

Conditions
ConditionsYield
Ansaeuern mit wss. HCl und Hydrieren des Reaktionsgemisches an Palladium;
(S)-methyl 5-amino-4-{[(benzyloxy)carbonyl]amino}-5-oxopentanoate
51163-40-7

(S)-methyl 5-amino-4-{[(benzyloxy)carbonyl]amino}-5-oxopentanoate

aqueous NaOH

aqueous NaOH

A

glutamine
636-65-7

glutamine

B

L-glutamine
56-85-9

L-glutamine

Conditions
ConditionsYield
Ansaeuern mit wss. HCl und Hydrieren des Reaktionsgemisches an Palladium;
N-lauroyl-L-glutamine

N-lauroyl-L-glutamine

A

lauric acid
143-07-7

lauric acid

B

L-glutamine
56-85-9

L-glutamine

Conditions
ConditionsYield
With acylase I from pig kidney; water In glycerol at 37℃; for 3h; pH=7.5; Equilibrium constant;
Conditions
ConditionsYield
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;
(R)-2-((E)-(R)-4-{(2S,3S)-2-[(S)-2-({(S)-1-[(S)-1-(2-Amino-acetyl)-pyrrolidine-2-carbonyl]-pyrrolidine-2-carbonyl}-amino)-4-carbamoyl-butyrylamino]-3-methyl-pentanoylamino}-6-methyl-hept-2-enoylamino)-3-(1H-indol-3-yl)-propionic acid

(R)-2-((E)-(R)-4-{(2S,3S)-2-[(S)-2-({(S)-1-[(S)-1-(2-Amino-acetyl)-pyrrolidine-2-carbonyl]-pyrrolidine-2-carbonyl}-amino)-4-carbamoyl-butyrylamino]-3-methyl-pentanoylamino}-6-methyl-hept-2-enoylamino)-3-(1H-indol-3-yl)-propionic acid

A

2-[(2E,4R)-4-amino-6-methylhept-2-enoylamino]-(2R)-3-(indol-3-yl)propanoic acid

2-[(2E,4R)-4-amino-6-methylhept-2-enoylamino]-(2R)-3-(indol-3-yl)propanoic acid

B

L-isoleucine
73-32-5

L-isoleucine

C

L-glutamine
56-85-9

L-glutamine

D

glycine
56-40-6

glycine

E

Pro

Pro

Conditions
ConditionsYield
With sodium phosphate buffer; leucine amino peptidase at 37℃; pH=7.2; Title compound not separated from byproducts;
(R)-2-((E)-(S)-4-{(2S,3S)-2-[(S)-2-({(S)-1-[(S)-1-(2-Amino-acetyl)-pyrrolidine-2-carbonyl]-pyrrolidine-2-carbonyl}-amino)-4-carbamoyl-butyrylamino]-3-methyl-pentanoylamino}-6-methyl-hept-2-enoylamino)-3-(1H-indol-3-yl)-propionic acid

(R)-2-((E)-(S)-4-{(2S,3S)-2-[(S)-2-({(S)-1-[(S)-1-(2-Amino-acetyl)-pyrrolidine-2-carbonyl]-pyrrolidine-2-carbonyl}-amino)-4-carbamoyl-butyrylamino]-3-methyl-pentanoylamino}-6-methyl-hept-2-enoylamino)-3-(1H-indol-3-yl)-propionic acid

A

2-[(2E,4S)-4-amino-6-methylhept-2-enoylamino]-(2R)-3-(indol-3-yl)propanoic acid

2-[(2E,4S)-4-amino-6-methylhept-2-enoylamino]-(2R)-3-(indol-3-yl)propanoic acid

B

L-isoleucine
73-32-5

L-isoleucine

C

L-glutamine
56-85-9

L-glutamine

D

glycine
56-40-6

glycine

E

Pro

Pro

Conditions
ConditionsYield
With sodium phosphate buffer; leucine amino peptidase at 37℃; pH=7.2; Title compound not separated from byproducts;
monosodium L-glutamate
142-47-2

monosodium L-glutamate

L-glutamine
56-85-9

L-glutamine

Conditions
ConditionsYield
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
30924-93-7

Boc-Glu-OBn

L-glutamine
56-85-9

L-glutamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: 1 N HCl, H2O / acetic acid / 0.83 h / 55 °C
View Scheme
L-glutamic acid dibenzyl ester hydrochloride
4561-10-8

L-glutamic acid dibenzyl ester hydrochloride

L-glutamine
56-85-9

L-glutamine

Conditions
ConditionsYield
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
56-85-9

L-glutamine

methyl 1-β-D-ribofuranosyl-1,2,4-triazole-3-carboximidate
120362-25-6

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
142633-85-0

1-β-D-ribofuranosyl-1,2,4-triazole-3-N-(α-carboxy-4'-butyramido)carboxamidine

Conditions
ConditionsYield
In methanol for 168h; Ambient temperature;100%
L-glutamine
56-85-9

L-glutamine

1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate
17720-18-2

1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate

1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate (S)-5-amino-2-ammonio-5-oxopentanoate

1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate (S)-5-amino-2-ammonio-5-oxopentanoate

Conditions
ConditionsYield
In water pH=4.95; Cooling with ice;100%
L-glutamine
56-85-9

L-glutamine

nicotinic acid riboside 5'-monophosphate

nicotinic acid riboside 5'-monophosphate

(S)-4-amino-1-carboxy-4-oxobutan-1-aminium 1-((2R,3R,4S,5R)-5-(((hydrogenphosphonato)oxy)methyl)-3,4-dihydrotetrahydrofuran-2-yl)pyridine-1-ium-3-carboxylate

(S)-4-amino-1-carboxy-4-oxobutan-1-aminium 1-((2R,3R,4S,5R)-5-(((hydrogenphosphonato)oxy)methyl)-3,4-dihydrotetrahydrofuran-2-yl)pyridine-1-ium-3-carboxylate

Conditions
ConditionsYield
In water at 10℃; pH=Ca. 2.3 - 2.5;100%
L-glutamine
56-85-9

L-glutamine

nicotinic acid riboside 5'-monophosphate

nicotinic acid riboside 5'-monophosphate

bis((S)-4-amino-1-carboxy-4-oxobutan-1-aminium)-1-((2R,3S,4R,5R)-3,4-dihydroxy-5-((phosphonatooxy)methyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate

bis((S)-4-amino-1-carboxy-4-oxobutan-1-aminium)-1-((2R,3S,4R,5R)-3,4-dihydroxy-5-((phosphonatooxy)methyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate

Conditions
ConditionsYield
In water at 10℃; pH=Ca. 2.8;100%
L-glutamine
56-85-9

L-glutamine

ethanolamine
141-43-5

ethanolamine

nicotinic acid riboside 5'-monophosphate

nicotinic acid riboside 5'-monophosphate

2-hydroxyethan-1-aminium (S)-4-amino-1-carboxy-4-oxobutan-1-aminium 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-((phosphonatooxy)methyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate

2-hydroxyethan-1-aminium (S)-4-amino-1-carboxy-4-oxobutan-1-aminium 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-((phosphonatooxy)methyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate

Conditions
ConditionsYield
In water pH=2.1 - 5.06; Inert atmosphere; Cooling with ice;100%
L-glutamine
56-85-9

L-glutamine

acetic anhydride
108-24-7

acetic anhydride

N-acetyl-L-glutamine
2490-97-3

N-acetyl-L-glutamine

Conditions
ConditionsYield
In water for 0.0666667h; Irradiation;99%
With sodium hydroxide
L-glutamine
56-85-9

L-glutamine

Z-Thr(But)-ONSu
10068-65-2

Z-Thr(But)-ONSu

Z-L-Thr(tBu)-L-Gln-OH
138541-15-8

Z-L-Thr(tBu)-L-Gln-OH

Conditions
ConditionsYield
With sodium hydrogencarbonate In 1,4-dioxane; water for 48h; Ambient temperature;99%
potassium hexachloropalladate

potassium hexachloropalladate

L-glutamine
56-85-9

L-glutamine

trans-Pd(L-Gln-O)2
119363-27-8

trans-Pd(L-Gln-O)2

Conditions
ConditionsYield
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
56-85-9

L-glutamine

α-carbobenzoxy-L-tryptophan p-nitrophenyl ester
16624-64-9

α-carbobenzoxy-L-tryptophan p-nitrophenyl ester

N-benzyloxycarbonyl-L-tryptophan-L-glutamine
1105050-57-4

N-benzyloxycarbonyl-L-tryptophan-L-glutamine

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; water at 20℃;99%
L-glutamine
56-85-9

L-glutamine

benzyl chloroformate
501-53-1

benzyl chloroformate

Cbz-L-Gln
2650-64-8

Cbz-L-Gln

Conditions
ConditionsYield
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
56-85-9

L-glutamine

N-Benzyloxycarbonyl-N-trifluoromethylsulfonyl-4-trifluoromethylanilide
250296-57-2

N-Benzyloxycarbonyl-N-trifluoromethylsulfonyl-4-trifluoromethylanilide

Cbz-L-Gln
2650-64-8

Cbz-L-Gln

Conditions
ConditionsYield
With water; triethylamine In 1,4-dioxane at 20℃; for 1h; Acylation;98%
L-glutamine
56-85-9

L-glutamine

(R)-N-(2-benzoyl-4-chlorophenyl)-1-[(3,4-dichlorophenyl)methyl]-2-pyrrolidinecarboxamide
1644308-43-9

(R)-N-(2-benzoyl-4-chlorophenyl)-1-[(3,4-dichlorophenyl)methyl]-2-pyrrolidinecarboxamide

nickel(II) acetate tetrahydrate
6018-89-9

nickel(II) acetate tetrahydrate

C30H27Cl3N4NiO4

C30H27Cl3N4NiO4

Conditions
ConditionsYield
With potassium carbonate In methanol at 60℃; for 3h; Temperature;98%
L-glutamine
56-85-9

L-glutamine

9-methoxy-9-BBN
38050-71-4

9-methoxy-9-BBN

(S)-3-(5'-oxo-9λ4-boraspiro[bicyclo[3.3.1]nonane-9,2'-[1,3,2]oxazaborolidin]-4'-yl)propanamide

(S)-3-(5'-oxo-9λ4-boraspiro[bicyclo[3.3.1]nonane-9,2'-[1,3,2]oxazaborolidin]-4'-yl)propanamide

Conditions
ConditionsYield
In methanol; hexane for 1h; Reflux;98%
manganese (II) nitrate tetrahydrate

manganese (II) nitrate tetrahydrate

L-glutamine
56-85-9

L-glutamine

Mn(OC(O)CH(NH2)CH2CH2C(O)NH2)2

Mn(OC(O)CH(NH2)CH2CH2C(O)NH2)2

Conditions
ConditionsYield
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%
L-glutamine
56-85-9

L-glutamine

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

Boc-Gln-OH
13726-85-7

Boc-Gln-OH

Conditions
ConditionsYield
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
56-85-9

L-glutamine

cholin hydroxide
123-41-1

cholin hydroxide

2-hydroxyethyltrimethylammonium L-glutaminate
1361335-92-3

2-hydroxyethyltrimethylammonium L-glutaminate

Conditions
ConditionsYield
In water at 3℃; for 48h; Darkness;95%
L-glutamine
56-85-9

L-glutamine

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

3-(5-oxo-1-phenyl-2-thioxoimidazolidin-4-yl)propanamide
29588-05-4

3-(5-oxo-1-phenyl-2-thioxoimidazolidin-4-yl)propanamide

Conditions
ConditionsYield
With triethylamine In water; N,N-dimethyl-formamide at 20℃; for 3h;95%
L-glutamine
56-85-9

L-glutamine

2,2-bis(4'-nitrophenyl)ethyl-N-succinimidyl carbonate
116869-01-3

2,2-bis(4'-nitrophenyl)ethyl-N-succinimidyl carbonate

Nα-<2,2-bis(4'-nitrophenyl)ethoxycarbonyl>-glutamine
138296-31-8

Nα-<2,2-bis(4'-nitrophenyl)ethoxycarbonyl>-glutamine

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane; water Ambient temperature;94%
Z-Lys(-Boc)-Osu
3338-34-9

Z-Lys(-Boc)-Osu

L-glutamine
56-85-9

L-glutamine

Z-Lys(Boc)-Gln-OH
68171-87-9

Z-Lys(Boc)-Gln-OH

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane at 0 - 20℃; for 123h;93%
L-glutamine
56-85-9

L-glutamine

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine
71989-20-3

N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine

Conditions
ConditionsYield
With sodium carbonate In 1,4-dioxane; water at 0 - 20℃;93%
With sodium carbonate In tetrahydrofuran; water84%
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
56-85-9

L-glutamine

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

5-amino-2(S)-{[(4-methylphenyl)sulfonyl]amino}-5-oxopentanoic acid
42749-49-5

5-amino-2(S)-{[(4-methylphenyl)sulfonyl]amino}-5-oxopentanoic acid

Conditions
ConditionsYield
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
56-85-9

L-glutamine

tetraethylammonium hydroxide
77-98-5

tetraethylammonium hydroxide

tetraethylammonium L-glutaminate
1248586-10-8

tetraethylammonium L-glutaminate

Conditions
ConditionsYield
In water at 20℃; for 2h;91%
L-glutamine
56-85-9

L-glutamine

2,7-disulfo-9-fluorenylmethoxycarbonyl chloride

2,7-disulfo-9-fluorenylmethoxycarbonyl chloride

C20H18N2O11S2(2-)*2Na(1+)

C20H18N2O11S2(2-)*2Na(1+)

Conditions
ConditionsYield
With sodium hydrogencarbonate In water at 20℃; for 0.5h; pH=8.5;90.8%
4-hydroxy[1]benzopyran-2-one
1076-38-6

4-hydroxy[1]benzopyran-2-one

L-glutamine
56-85-9

L-glutamine

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

N-(methylene-4-oxocoumarinyl)-L-glutamine

N-(methylene-4-oxocoumarinyl)-L-glutamine

Conditions
ConditionsYield
In isopropyl alcohol for 2h; Heating;90%
L-glutamine
56-85-9

L-glutamine

3,5-dinitro-1-(4-nitrophenyl)-4-pyridone
74197-40-3

3,5-dinitro-1-(4-nitrophenyl)-4-pyridone

A

4-nitro-aniline
100-01-6

4-nitro-aniline

B

(S)-4-Carbamoyl-2-(3,5-dinitro-4-oxo-4H-pyridin-1-yl)-butyric acid

(S)-4-Carbamoyl-2-(3,5-dinitro-4-oxo-4H-pyridin-1-yl)-butyric acid

Conditions
ConditionsYield
In pyridine; water for 2h; Ambient temperature;A n/a
B 90%
L-glutamine
56-85-9

L-glutamine

benzyl (4-(chlorocarbonyl)phenyl)(methyl)carbamate
66891-86-9

benzyl (4-(chlorocarbonyl)phenyl)(methyl)carbamate

N2-<4-<<(benzyloxy)carbonyl>methylamino>benzoyl>-L-glutamine
96845-85-1

N2-<4-<<(benzyloxy)carbonyl>methylamino>benzoyl>-L-glutamine

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane at 0 - 5℃;90%
L-glutamine
56-85-9

L-glutamine

ethylamine
75-04-7

ethylamine

Conditions
ConditionsYield
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;

56-85-9Relevant articles and documents

A PROCESS FOR THE PREPARATION OF L-GLUTAMINE

-

Page/Page column 13; 14; 15; 16, (2022/01/24)

The present invention relates to a process for the preparation of L-Glutamine of Formula (I). The present invention also relates to an improved process for the purification of L-Glutamine of Formula (I) having specific bulk density and Hausner ratio.

A novel strategy for efficient chemoenzymatic synthesis of D-glutamine using recombinant Escherichia coli cells

Du, Qinglin,Zhang, Xiangyang,Pan, Xinru,Zhang, Hongjuan,Yang, Yu-Shun,Liu, Junzhong,Jiao, Qingcai

, (2020/06/17)

D-glutamine is a D type stereoisomer of glutamine which is involved in many metabolic processes. Seeking lower-cost and industrially scalable approaches for the synthesis of D-glutamine is very valuable both in academic career and potential applications. Herein, we developed a novel efficient chemoenzymatic strategy for producing D-glutamine. Initially, DL-glutamine was chemically prepared with cheap and accessible DL-glutamic acid as raw material. Subsequently, the L-glutamine among the racemic mixture was selectively hydrolyzed to L-glutamic acid by Escherichia coli whole-cell system which expressed L-aminopeptidase D-Ala-esterase/amidase (DmpA) from Ochrobactrum anthropi. The left D-glutamine was obtained by isoelectric point precipitation with 70% of the theoretical yield. Furthermore, we optimized enzymatic resolution conditions to determine the optimum parameters as pH 8, 30 °C, 0.1% (v/v) Triton X-100, and 1 mM Mn2+. These results suggested that our strategy might be potentially usable for the synthesis of D-glutamine in industrial productions.

Substrate Specificity and Chemical Mechanism for the Reaction Catalyzed by Glutamine Kinase

Taylor, Zane W.,Chamberlain, Alexandra R.,Raushel, Frank M.

, (2018/09/21)

Campylobacter jejuni, a leading cause of gastroenteritis worldwide, has a unique O-methyl phosphoramidate (MeOPN) moiety attached to its capsular polysaccharide. Investigations into the biological role of MeOPN have revealed that it contributes to the pathogenicity of C. jejuni, and this modification is important for the colonization of C. jejuni. Previously, the reactions catalyzed by four enzymes (Cj1418-Cj1415) from C. jejuni that are required for the biosynthesis of the phosphoramidate modification have been elucidated. Cj1418 (l-glutamine kinase) catalyzes the formation of the initial phosphoramidate bond with the ATP-dependent phosphorylation of the amide nitrogen of l-glutamine. Here we show that Cj1418 catalyzes the phosphorylation of l-glutamine through a three-step reaction mechanism via the formation of covalent pyrophosphorylated (Enz-X-Pβ-Pγ) and phosphorylated (Enz-X-Pβ) intermediates. In the absence of l-glutamine, the enzyme was shown to catalyze a positional isotope exchange (PIX) reaction within β-[18O4]-ATP in support of the formation of the Enz-X-Pβ-Pγintermediate. In the absence of ATP, the enzyme was shown to catalyze a molecular isotope exchange (MIX) reaction between l-glutamine phosphate and [15N-amide]-l-glutamine in direct support of the Enz-X-Pβintermediate. The active site nucleophile has been identified as His-737 based on the lack of activity of the H737N mutant and amino acid sequence comparisons. The enzyme was shown to also catalyze the phosphorylation of d-glutamine, γ-l-glutamyl hydroxamate, γ-l-glutamyl hydrazide, and β-l-aspartyl hydroxamate, in addition to l-glutamine.

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