• Name

  L-Alanyl-L-Glutamine

• EINECS 475-290-9
• CAS No. 39537-23-0
• Article Data12
• CAS DataBase
• Density 1.305g/cm³
• Solubility Soluble in water.
• Melting Point 215 °C
• Formula C₈H₁₅N₃O₄
• Boiling Point 615.4 °C at 760 mmHg
• Molecular Weight 217.225
• Flash Point 326 °C
• Transport Information
• Appearance
• Safety 23-24/25-36-26
• Risk Codes 36/37/38
• Molecular Structure
• Hazard Symbols Xi
• Synonyms Glutamine,N2-L-alanyl- (7CI);L-Glutamine, N2-L-alanyl-;Dipeptamin;Dipeptiven;GlutaMAX;L-Ala-L-Gln;L-Alanyl-L-glutamine;Glutamax I;
• PSA 135.51000
• LogP -0.04000

Synthetic route

2-bromopropionyl-L-glutamine

39537-23-0

alanylglutamine

Conditions

Conditions	Yield
With ammonium hydroxide at 20 - 60℃; for 8h; Autoclave;	99.8%

56-85-9

L-glutamine

1142-20-7

N-Cbz-Ala

39537-23-0

alanylglutamine

Conditions

Conditions	Yield
Stage #1: N-Cbz-Ala With hexachloroethane; triphenylphosphine In tetrahydrofuran at 0℃; for 1.5h; Stage #2: L-glutamine With potassium hydroxide In tetrahydrofuran; dichloromethane; water at 0℃; for 2h; pH=13; Stage #3: With sulfuric acid; hydrogen Product distribution / selectivity; more than 3 stages;	65%
Stage #1: N-Cbz-Ala With hexachloroethane; triphenylphosphine In toluene at 0℃; for 3h; Stage #2: L-glutamine With sodium hydroxide In water; toluene at 15℃; for 1.5h; pH=12; Stage #3: With hydrogenchloride; hydrogen Product distribution / selectivity; more than 3 stages;	48%
Stage #1: N-Cbz-Ala With hexachloroethane; triphenylphosphine In acetonitrile at 5℃; for 1h; Stage #2: L-glutamine With sodium hydroxide; potassium carbonate In water; acetonitrile at 5℃; for 2h; pH=10; Stage #3: With hydrogenchloride; trifluoroacetic acid Product distribution / selectivity; more than 3 stages;	45%

N-(O,O-diethyl) phosphoalanine

56-85-9

L-glutamine

39537-23-0

alanylglutamine

Conditions

Conditions	Yield
Stage #1: N-(O,O-diethyl) phosphoalanine With hexachloroethane; triphenylphosphine In dichloromethane at 0℃; for 0.666667h; Stage #2: L-glutamine With potassium hydroxide In dichloromethane; cyclohexane; water at 20℃; for 0.5h; pH=13; Stage #3: With nitric acid; trifluoroacetic acid Product distribution / selectivity; more than 3 stages;	60%
Stage #1: N-(O,O-diethyl) phosphoalanine With hexachloroethane; triphenylphosphine In acetonitrile at 15℃; for 2.5h; Stage #2: L-glutamine With sodium carbonate In water; toluene; acetonitrile at 30℃; for 1h; pH=8.5; Stage #3: With sulfuric acid; hydrogen bromide Product distribution / selectivity; more than 3 stages;	40%

56-85-9

L-glutamine

5872-22-0

N-pivaloylalanine

39537-23-0

alanylglutamine

Conditions

Conditions	Yield
Stage #1: N-pivaloylalanine With hexachloroethane; triphenylphosphine In toluene at 5℃; for 2h; Stage #2: L-glutamine With sodium hydroxide In water; toluene; Petroleum ether at 10℃; for 1.5h; pH=12; Stage #3: With hydrogenchloride; sulfuric acid Product distribution / selectivity; more than 3 stages;	52%
Stage #1: N-pivaloylalanine With hexachloroethane; triphenylphosphine In tetrahydrofuran at 0℃; for 1.5h; Stage #2: L-glutamine With potassium hydroxide; sodium carbonate In tetrahydrofuran; dichloromethane; water at 8℃; for 2h; pH=10; Stage #3: With hydrogenchloride; methanesulfonic acid Product distribution / selectivity; more than 3 stages;	45%
Stage #1: N-pivaloylalanine With hexachloroethane; triphenylphosphine In 1,2-dichloro-ethane at 10℃; for 0.333333h; Stage #2: L-glutamine With potassium hydroxide In cyclohexane; water; 1,2-dichloro-ethane at 20℃; for 0.5h; pH=11; Stage #3: With nitric acid; trifluoroacetic acid Product distribution / selectivity; more than 3 stages;	40%

N-(O,O-diisopropyl) phosphoalanine

56-85-9

L-glutamine

39537-23-0

alanylglutamine

Conditions

Conditions	Yield
Stage #1: N-(O,O-diisopropyl) phosphoalanine With hexachloroethane; triphenylphosphine In 1,2-dichloro-ethane at 20℃; for 1.5h; Stage #2: L-glutamine With potassium hydroxide In water; 1,2-dichloro-ethane at 10℃; for 2h; pH=13; Stage #3: With nitric acid; trifluoroacetic acid Product distribution / selectivity; more than 3 stages;	52%
Stage #1: N-(O,O-diisopropyl) phosphoalanine With hexachloroethane; triphenylphosphine In dichloromethane at 10℃; for 3h; Stage #2: L-glutamine With sodium hydroxide; sodium carbonate In dichloromethane; water; ethyl acetate at 10℃; for 1h; pH=9; Stage #3: With sulfuric acid; hydrogen bromide Product distribution / selectivity; more than 3 stages;	45%

N-(O,O-dimethyl) phosphoalanine

56-85-9

L-glutamine

39537-23-0

alanylglutamine

Conditions

Conditions	Yield
Stage #1: N-(O,O-dimethyl) phosphoalanine With hexachloroethane; triphenylphosphine In tetrahydrofuran at 10℃; for 0.333333h; Stage #2: L-glutamine With sodium hydroxide In tetrahydrofuran; cyclohexane; water at 25℃; for 0.5h; pH=12; Stage #3: With hydrogen bromide; nitric acid Product distribution / selectivity; more than 3 stages;	50%
Stage #1: N-(O,O-dimethyl) phosphoalanine With hexachloroethane; triphenylphosphine In dichloromethane; toluene at 0℃; for 3h; Stage #2: L-glutamine With potassium hydroxide; potassium hydrogencarbonate In dichloromethane; water; toluene; Petroleum ether at 0℃; for 1.5h; pH=10; Stage #3: With hydrogenchloride; methanesulfonic acid Product distribution / selectivity; more than 3 stages;	45%
Stage #1: N-(O,O-dimethyl) phosphoalanine With hexachloroethane; triphenylphosphine In toluene at 5℃; for 1h; Stage #2: L-glutamine With sodium carbonate In ethanol; water; toluene at 5℃; for 0.166667h; pH=9.5; Stage #3: With phosphoric acid; trifluoroacetic acid Product distribution / selectivity; more than 3 stages;	40%

90770-50-6

L-Alanyl-<γ-methyl>-L-glutamat

39537-23-0

alanylglutamine

Conditions

Conditions	Yield
With ammonium hydroxide

4652-65-7

(S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-methyl ester

39537-23-0

alanylglutamine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: Et3N / ethyl acetate / Heating 2: aq. HBr / acetic acid 3: DCC / ethyl acetate 4: H2 / Pd-C / methanol; H2O 5: aq. NH3 View Scheme

96789-24-1

α-p-Nitro-benzyl-γ-methyl-L-glutamat

39537-23-0

alanylglutamine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: DCC / ethyl acetate 2: H2 / Pd-C / methanol; H2O 3: aq. NH3 View Scheme

N-Carbobenzoxy-<α-p-nitro-benzyl,γ-methyl>-L-glutamat

910908-63-3

N-Carbobenzoxy-<α-p-nitro-benzyl,γ-methyl>-L-glutamat

39537-23-0

alanylglutamine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: aq. HBr / acetic acid 2: DCC / ethyl acetate 3: H2 / Pd-C / methanol; H2O 4: aq. NH3 View Scheme

39537-23-0

alanylglutamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: H2 / Pd-C / methanol; H2O 2: aq. NH3 View Scheme

Z-Ala-Gln-OH

Z-Ala-Gln-OH

39537-23-0

alanylglutamine

Conditions

Conditions	Yield
palladium In methanol; water

L-glutamine

2491-20-5

L-alanine methyl ester hydrochloride

39537-23-0

alanylglutamine

Conditions

Conditions	Yield
With α-amino acid ester acyl transferase from Empedobacter brevis ATCC14234 at 25℃; for 0.166667h; pH=9; Kinetics; borate buffer; Enzymatic reaction;

2-chloropropionyl-L-glutamine

39537-23-0

alanylglutamine

Conditions

Conditions	Yield
With ammonia In water
With ammonium hydroxide at 20 - 60℃; for 9h; Autoclave;	42.5 g

N-(α-chloro)propionyl-L-glutamine

39537-23-0

alanylglutamine

Conditions

Conditions	Yield
With ammonium hydroxide In water at 60℃; under 1500.15 Torr;

39537-23-0

alanylglutamine

66-22-8

uracil

platinum(II) chloride

C12H17N5O6Pt

Conditions

Conditions	Yield
In neat (no solvent, solid phase) at 80℃; for 36h;	87%

...Expand

553-26-4

4,4'-bipyridine

39537-23-0

alanylglutamine

6046-93-1

copper(II) acetate monohydrate

[Cu2(4,4'-bipyridine)(N-(2)-L-alanyl-L-glutamine-2H)2(H2O)2]•8H2O

Conditions

Conditions	Yield
Stage #1: alanylglutamine; copper(II) acetate monohydrate In methanol at 49.84℃; for 4h; pH=6.5; Stage #2: 4,4'-bipyridine In methanol at 49.84℃; for 24h;	69.26%

...Expand

39537-23-0

alanylglutamine

77-76-9

2,2-dimethoxy-propane

Ala-Gln-OMe

Conditions

Conditions	Yield
With hydrogenchloride at 20℃;

39537-23-0

alanylglutamine

952312-55-9

C12H19N3O5

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. HCl / 20 °C 2: dimethylformamide / -10 - 20 °C View Scheme

39537-23-0

alanylglutamine

C47H55N3O10

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: aq. HCl / 20 °C 2: dimethylformamide / -10 - 20 °C 3: 46 percent / substituted Grubbs-type ruthenium carbene complex / CH2Cl2 / 18 h / 40 °C View Scheme

39537-23-0

alanylglutamine

140945-56-8

N-propionyl-L-alanyl-L-glutamine

Conditions

Conditions	Yield
In tetrahydrofuran; sodium hydroxide

sodium metavanadate

39537-23-0

alanylglutamine

(L-alanine-glutamine)(x)V2O5*H2O

Conditions

Conditions	Yield
In water acidification of aq. soln. of NaVO3 to pH=1.4 by DOWEX 50 WX proton exchange resin; solid dipeptide added, soln. aged for 24 h at room temp. in closed vessel; ppt. filtered, rinsed twice with deionised H2O, dried at room temp. for 24 h;

39537-23-0

alanylglutamine

110484-60-1, 118174-70-2

(S)-2-((diisopropoxyphosphoryl)amino)propanoic acid

290312-62-8

Ala-Ala-Gln

Conditions

Conditions	Yield
In water at 37℃; for 24h; pH=7.4; Mechanism; aq. buffer;

39537-23-0

alanylglutamine

A

56-41-7

L-alanin

B

56-85-9

L-glutamine

Conditions

Conditions	Yield
With recombinant Streptomyces coelicolor Sco3058 dipeptidase; water at 30℃; pH=8; Kinetics; Concentration; aq. buffer; Enzymatic reaction;

zinc(II) sulfate heptahydrate

39537-23-0

alanylglutamine

Ala-Gln dipeptide-Zn2+ complex

Conditions

Conditions	Yield
In water at 60℃; for 1.5h;

39537-23-0

alanylglutamine

alanyl-alanyl-glutamine

Alanyl-glutamine Chemical Properties

  MF: C₈H₁₅N₃O₄
  MW: 217.22
  Alanyl glutamine,its melting point is  215 °C,appearance is White or off white crystalline powder .
  Following is the molecular structure of Alanyl glutamine:
  

Alanyl-glutamine Uses

Alanyl-glutamine Safety Profile