Record Information
Version 1.0
Update Date 1/22/2018 11:54:53 AM
Metabolite IDPAMDB000163
Identification
Name: L-Glutamine
Description:Glutamine (Gln) is one of the 20 amino acids encoded by the standard genetic code. Its side chain is an amide; it is formed by replacing a side-chain hydroxyl of glutamic acid with an amine functional group. Glutamine has a variety of biochemical functions including: 1. As any other amino acid, a major role in protein synthesis. 2. Cellular energy source, next to glucose. 3. Nitrogen donor for many anabolic processes. 4.Carbon source, refilling the Citric acid cycle. (Wikipedia)
Structure
Thumb
Synonyms:
  • (2S)-2,5-diamino-5-oxopentanoate
  • (2S)-2,5-diamino-5-oxopentanoic acid
  • (2S)-2-amino-4-carbamoylbutanoate
  • (2S)-2-amino-4-carbamoylbutanoic acid
  • (S)-2,5-Diamino-5-oxopentanoate
  • (S)-2,5-Diamino-5-oxopentanoic acid
  • 2-Aminoglutaramate
  • 2-Aminoglutaramic acid
  • Cebrogen
  • g-Glutamine
  • Gamma-Glutamine
  • Glavamin
  • Gln
  • Glum
  • Glumin
  • Glutamate 5-amide
  • Glutamate amide
  • Glutamic acid 5-amide
  • Glutamic acid amide
  • Glutamine
  • L-(+)-Glutamine
  • L-2-Aminoglutaramate
  • L-2-Aminoglutaramic acid
  • L-2-Aminoglutaramidate
  • L-2-Aminoglutaramidic acid
  • L-Glutamate 5-amide
  • L-Glutamate g-amide
  • L-Glutamate gamma-amide
  • L-Glutamate γ-amide
  • L-Glutamic acid 5-amide
  • L-Glutamic acid g-amide
  • L-Glutamic acid gamma-amide
  • L-Glutamic acid γ-amide
  • L-Glutamid
  • L-Glutamide
  • L-Glutamin
  • L-Glutamine
  • L-Glutaminsaeure-5-amid
  • Levoglutamid
  • Levoglutamida
  • Levoglutamide
  • Levoglutamidum
  • Levoglutamina
  • Polyglutamine
  • Proglumide
  • Q
  • Stimulina
  • γ-Glutamine
Chemical Formula: C5H10N2O3
Average Molecular Weight: 146.1445
Monoisotopic Molecular Weight: 146.069142196
InChI Key: ZDXPYRJPNDTMRX-VKHMYHEASA-N
InChI: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
CAS number: 56-85-9
IUPAC Name:(2S)-2-amino-4-carbamoylbutanoic acid
Traditional IUPAC Name: L-glutamine
SMILES:N[C@@H](CCC(N)=O)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct Parent L-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • Fatty amide
  • Primary carboxylic acid amide
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: 185 °C
Experimental Properties:
PropertyValueSource
Water Solubility:41.3 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; 41.3 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP:-3.64 [CHMELIK,J ET AL. (1991)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility97.8 mg/mLALOGPS
logP-3.3ALOGPS
logP-4ChemAxon
logS-0.17ALOGPS
pKa (Strongest Acidic)2.15ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area106.41 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity33.11 m3·mol-1ChemAxon
Polarizability13.87 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
2 Adenosine triphosphate + L-Glutamine + Water + Hydrogen carbonate >2 ADP + Carbamoylphosphate + L-Glutamate +2 Hydrogen ion + Phosphate
Adenosine triphosphate + Water + L-Glutamine > ADP + L-Glutamine + Hydrogen ion + Phosphate
Adenosine triphosphate + Water + L-Glutamine > ADP + L-Glutamine + Hydrogen ion + Phosphate
Chorismate + L-Glutamine <> 2-Aminobenzoic acid + L-Glutamate + Hydrogen ion + Pyruvic acid
L-Glutamine + Water > L-Glutamate + Ammonium
L-Glutamine + Phosphoribulosylformimino-AICAR-P > Phosphoribosyl formamidocarboxamide + D-Erythro-imidazole-glycerol-phosphate + L-Glutamate + Hydrogen ion
Chorismate + L-Glutamine <> 4-Amino-4-deoxychorismate + L-Glutamate
Adenosine triphosphate + L-Glutamate + Ammonium > ADP + L-Glutamine + Hydrogen ion + Phosphate
L-Aspartic acid + Adenosine triphosphate + L-Glutamine + Water > Adenosine monophosphate + L-Asparagine + L-Glutamate + Hydrogen ion + Pyrophosphate
Adenosine triphosphate + L-Glutamine + tRNA(Gln) > Adenosine monophosphate + L-Glutaminyl-tRNA(Gln) + Pyrophosphate
Adenosine triphosphate + L-Glutamine + Water + Xanthylic acid > Adenosine monophosphate + L-Glutamate + Guanosine monophosphate +2 Hydrogen ion + Pyrophosphate
Adenosine triphosphate + 5'-Phosphoribosyl-N-formylglycineamide + L-Glutamine + Water <> ADP + Phosphoribosylformylglycineamidine + L-Glutamate + Hydrogen ion + Phosphate
Adenosine triphosphate + L-Glutamine + Water + Uridine triphosphate > ADP + Cytidine triphosphate + L-Glutamate +2 Hydrogen ion + Phosphate
Fructose 6-phosphate + L-Glutamine <> Glucosamine 6-phosphate + L-Glutamate
2 L-Glutamate + NAD <> L-Glutamine + alpha-Ketoglutarate + NADH + Hydrogen ion
2 L-Glutamate + NADP <> L-Glutamine + alpha-Ketoglutarate + NADPH + Hydrogen ion
Adenosine triphosphate + L-Glutamate + Ammonia <> ADP + Phosphate + L-Glutamine
L-Glutamine + Water <> L-Glutamate + Ammonia
Adenosine triphosphate + Uridine triphosphate + L-Glutamine + Water <> ADP + Phosphate + Cytidine triphosphate + L-Glutamate
2 Adenosine triphosphate + L-Glutamine + Hydrogen carbonate + Water <>2 ADP + Phosphate + L-Glutamate + Carbamoylphosphate
Adenosine triphosphate + L-Aspartic acid + L-Glutamine + Water <> Adenosine monophosphate + Pyrophosphate + L-Asparagine + L-Glutamate
Chorismate + L-Glutamine <> 2-Aminobenzoic acid + Pyruvic acid + L-Glutamate
Adenosine triphosphate + Xanthylic acid + L-Glutamine + Water <> Adenosine monophosphate + Pyrophosphate + Guanosine monophosphate + L-Glutamate
Adenosine triphosphate + L-Glutamine + tRNA(Gln) + tRNA(Gln) <> Adenosine monophosphate + Pyrophosphate + Glutaminyl-tRNA + Glutaminyl-tRNA
Adenosine triphosphate + 5'-Phosphoribosyl-N-formylglycineamide + L-Glutamine + Water <> ADP + Phosphate + Phosphoribosylformylglycineamidine + L-Glutamate
Phosphoribulosylformimino-AICAR-P + L-Glutamine <> D-Erythro-imidazole-glycerol-phosphate + AICAR + L-Glutamate
6-Thioxanthine 5'-monophosphate + Adenosine triphosphate + L-Glutamine + Water <> 6-Thioguanosine monophosphate + Adenosine monophosphate + Pyrophosphate + L-Glutamate
-->-->L-Glutamate + NADP < Hydrogen ion + L-Glutamine + Oxoglutaric acid + NADPH
Phosphoribulosylformimino-AICAR-P + L-Glutamine > Hydrogen ion + L-Glutamate + D-Erythro-imidazole-glycerol-phosphate + AICAR
L-Glutamine + Water > Hydrogen ion + L-Glutamate + Ammonia
Adenosine triphosphate + Nicotinic acid adenine dinucleotide + L-Glutamine + Water > Hydrogen ion + Adenosine monophosphate + Pyrophosphate + NAD + L-Glutamate
5-Phosphoribosylamine + Pyrophosphate + L-Glutamate < Phosphoribosyl pyrophosphate + L-Glutamine + Water
ala-gln + Water > L-Alanine + L-Glutamine
gly-gln + Water > Glycine + L-Glutamine
2 Adenosine triphosphate + L-Glutamine + Carbonic acid + Water >2 ADP + Inorganic phosphate + L-Glutamate + Carbamoylphosphate
Adenosine triphosphate + L-Glutamate + Ammonia > ADP + Inorganic phosphate + L-Glutamine
2 L-Glutamate + NADP > L-Glutamine + Oxoglutaric acid + NADPH
Adenosine triphosphate + Uridine triphosphate + L-Glutamine + Water + Ammonia <> ADP + Phosphate + Cytidine triphosphate + L-Glutamate
2 Adenosine triphosphate + L-Glutamine + Hydrogen carbonate + Water + Ammonia + Carbamic acid + Carboxyphosphate <>2 ADP + Phosphate + L-Glutamate + Carbamoylphosphate
2 L-Glutamate + NADP + Ammonia + Water <> L-Glutamine + alpha-Ketoglutarate + NADPH + Hydrogen ion
Adenosine triphosphate + L-Aspartic acid + L-Glutamine + Water + Ammonia <> Adenosine monophosphate + Pyrophosphate + L-Asparagine + L-Glutamate
Adenosine triphosphate + Xanthylic acid + L-Glutamine + Water + Ammonia <> Adenosine monophosphate + Pyrophosphate + Guanosine monophosphate + L-Glutamate
Ammonia + L-Glutamic acid + Adenosine triphosphate + Oxoglutaric acid + L-Glutamate <> Phosphate + L-Glutamine + Adenosine diphosphate + ADP
L-Glutamic acid + Adenosine triphosphate + Ammonium + L-Glutamate > L-Glutamine + Hydrogen ion + Adenosine diphosphate + Phosphate + ADP
2 L-Glutamic acid + NADP + 2 L-Glutamate > L-Glutamine + NADPH + Hydrogen ion + Oxoglutaric acid + NADPH
L-Glutamine + Water > L-Glutamic acid + Ammonia + L-Glutamate
Adenosine triphosphate + L-Aspartic acid + L-Glutamine + Water + L-Aspartic acid > Adenosine monophosphate + Pyrophosphate + L-Asparagine + L-Glutamic acid + L-Asparagine + L-Glutamate
Hydrogen carbonate + Water + L-Glutamine + 2 Adenosine triphosphate >2 Adenosine diphosphate + Phosphate + L-Glutamic acid +2 Hydrogen ion + Carbamoylphosphate +2 ADP + L-Glutamate
L-Glutamine + Adenosine triphosphate + Hydrogen ion + tRNA(Gln) > Adenosine diphosphate + Pyrophosphate + L-Glutaminyl-tRNA(Gln) + ADP
Phosphoribulosylformimino-AICAR-P + L-Glutamine > L-Glutamic acid + Hydrogen ion + 5-Amino-4-imidazolecarboxyamide + D-Erythro-imidazole-glycerol-phosphate + L-Glutamate
L-Aspartic acid + Water + Adenosine triphosphate + L-Glutamine + L-Aspartic acid > L-Asparagine + Hydrogen ion + Adenosine monophosphate + L-Glutamic acid + Pyrophosphate + L-Asparagine + L-Glutamate
Chorismate + L-Glutamine > L-Glutamic acid + Pyruvic acid + Hydrogen ion + 2-Aminobenzoic acid + L-Glutamate
Nicotinic acid adenine dinucleotide + Water + L-Glutamine + Adenosine triphosphate > Hydrogen ion + Adenosine monophosphate + Pyrophosphate + L-Glutamic acid + NAD + L-Glutamate
D-tagatofuranose 6-phosphate + L-Glutamine <> Glucosamine 6-phosphate + L-Glutamic acid + L-Glutamate
Fructose 6-phosphate + L-Glutamine + Fructose 6-phosphate > L-Glutamic acid + Glucosamine 6-phosphate + L-Glutamate
Chorismate + L-Glutamine > L-Glutamic acid + 4-amino-4-deoxychorismate + L-Glutamate + 4-Amino-4-deoxychorismate
Phosphoribosyl pyrophosphate + Water + L-Glutamine > 5-Phosphoribosylamine + L-Glutamic acid + Pyrophosphate + 5-Phosphoribosylamine + L-Glutamate
5'-Phosphoribosyl-N-formylglycinamide + Water + L-Glutamine + Adenosine triphosphate + 5'-Phosphoribosyl-N-formylglycineamide > 2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidine + L-Glutamic acid + Phosphate + Adenosine diphosphate + Hydrogen ion + L-Glutamate + ADP
Xanthylic acid + Adenosine triphosphate + L-Glutamine + Water > Adenosine monophosphate + Pyrophosphate + L-Glutamic acid +2 Hydrogen ion + Guanosine monophosphate + L-Glutamate
Uridine triphosphate + L-Glutamine + Water + Adenosine triphosphate + Uridine triphosphate > Adenosine diphosphate + Hydrogen ion + Phosphate + L-Glutamic acid + Cytidine triphosphate + ADP + L-Glutamate
L-Glutamine + Adenosine triphosphate + Water > Adenosine diphosphate + Phosphate + Hydrogen ion + L-Glutamine + ADP
L-Glutamine + Adenosine triphosphate + Water > Adenosine diphosphate + Phosphate + Hydrogen ion + L-Glutamine + ADP
More...

Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0a4i-0910000000-adb283bb40327f705680View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0a4i-0910000000-134e80840320dadf6ad1View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-05fr-7910000000-89f87d4acc18299244f5View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0a4i-0900000000-952a471cad5e5ead0a7eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-004i-1961000000-94183211889cfe72d4ffView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0a4i-1920000000-6505cd814f3707a0febaView in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-004i-0692000000-9788416fdefb051b9586View in MoNA
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0059-3900000000-c8f487d1a561e49327c0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9000000000-eee04836e7577e11d0d0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a59-9000000000-54ffbe5be8d7dbede389View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-0900000000-79283391c985f8286677View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-9000000000-6afbd5929b6e2371a371View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-d5bd83614703b048228eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-dc8def340a2655f9a399View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-0900000000-47e3e94a4387c53e0bd6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-9000000000-c1acfa3750a90d81ce15View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-0900000000-93f01bccbc98f18d4b07View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-ce03708ec9ce55cd8952View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-0933201000-9339494cebedd9c39135View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0900000000-64561a4c3590d5994e37View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-0900000000-fdcdd7591fb182d804e2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03dm-0030900000-66314ae704783630947aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-0933100000-8798d2e46a415bb1029aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0900000000-dddea137e500a9b364ccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-0900000000-a78f8e4b2d6b37917b21View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-0920000000-8c6e1eb7de6f70911080View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-fa42fc4bcba608992804View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-2900000000-074610880ea19a417f60View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-059x-9200000000-8b7dae54eb8325667bd7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-e115d9215eea3f0c3629View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-55b1ac62eea66274b984View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001j-0900000000-c9c71895033d66cb2becView in MoNA
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-bc4e294b8a3fd8c5abceView in MoNA
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
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  • Rutten EP, Engelen MP, Wouters EF, Schols AM, Deutz NE: Metabolic effects of glutamine and glutamate ingestion in healthy subjects and in persons with chronic obstructive pulmonary disease. Am J Clin Nutr. 2006 Jan;83(1):115-23. Pubmed: 16400059
  • Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. Pubmed: 12097436
  • Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  • Subramanian A, Gupta A, Saxena S, Gupta A, Kumar R, Nigam A, Kumar R, Mandal SK, Roy R: Proton MR CSF analysis and a new software as predictors for the differentiation of meningitis in children. NMR Biomed. 2005 Jun;18(4):213-25. Pubmed: 15627241
  • Szebenyi G, Morfini GA, Babcock A, Gould M, Selkoe K, Stenoien DL, Young M, Faber PW, MacDonald ME, McPhaul MJ, Brady ST: Neuropathogenic forms of huntingtin and androgen receptor inhibit fast axonal transport. Neuron. 2003 Sep 25;40(1):41-52. Pubmed: 14527432
  • van der Hulst RR, von Meyenfeldt MF, Deutz NE, Soeters PB: Glutamine extraction by the gut is reduced in depleted [corrected] patients with gastrointestinal cancer. Ann Surg. 1997 Jan;225(1):112-21. Pubmed: 8998127
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Vijayendran, C., Barsch, A., Friehs, K., Niehaus, K., Becker, A., Flaschel, E. (2008). "Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling." Genome Biol 9:R72. Pubmed: 18402659
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  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference: Jiao, Qingcai; Qian, Shaosong; Chen, Ran; Wu, Xiaoyan. Synthesis of L-glutamine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 7 pp.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID18050
HMDB IDHMDB00641
Pubchem Compound ID5961
Kegg IDC00064
ChemSpider ID5746
WikipediaL-Glutamine
BioCyc IDGLN
EcoCyc IDGLN
Ligand ExpoGLN_LFZW

Enzymes

General function:
Involved in asparaginase activity
Specific function:
L-asparagine + H(2)O = L-aspartate + NH(3)
Gene Name:
ansB
Locus Tag:
PA1337
Molecular weight:
38.6 kDa
Reactions
L-asparagine + H(2)O = L-aspartate + NH(3).
General function:
Involved in biosynthetic process
Specific function:
Chorismate + L-glutamine = anthranilate + pyruvate + L-glutamate
Gene Name:
trpE
Locus Tag:
PA0609
Molecular weight:
54.6 kDa
Reactions
Chorismate + L-glutamine = anthranilate + pyruvate + L-glutamate.
General function:
Involved in metabolic process
Specific function:
Catalyzes the biosynthesis of 4-amino-4-deoxychorismate (ADC) from chorismate and glutamine
Gene Name:
pabA
Locus Tag:
PA0649
Molecular weight:
22 kDa
Reactions
Chorismate + L-glutamine = 4-amino-4-deoxychorismate + L-glutamate.
General function:
Involved in anthranilate phosphoribosyltransferase activity
Specific function:
Chorismate + L-glutamine = anthranilate + pyruvate + L-glutamate
Gene Name:
trpD
Locus Tag:
PA0650
Molecular weight:
37.4 kDa
Reactions
Chorismate + L-glutamine = anthranilate + pyruvate + L-glutamate.
N-(5-phospho-D-ribosyl)-anthranilate + diphosphate = anthranilate + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in nucleotide binding
Specific function:
ATP + L-glutamine + tRNA(Gln) = AMP + diphosphate + L-glutaminyl-tRNA(Gln)
Gene Name:
glnS
Locus Tag:
PA1794
Molecular weight:
62.9 kDa
Reactions
ATP + L-glutamine + tRNA(Gln) = AMP + diphosphate + L-glutaminyl-tRNA(Gln).
General function:
Involved in ATP binding
Specific function:
2 ATP + L-glutamine + HCO(3)(-) + H(2)O = 2 ADP + phosphate + L-glutamate + carbamoyl phosphate
Gene Name:
carB
Locus Tag:
PA4756
Molecular weight:
117.3 kDa
Reactions
2 ATP + L-glutamine + HCO(3)(-) + H(2)O = 2 ADP + phosphate + L-glutamate + carbamoyl phosphate.
General function:
Involved in GMP synthase (glutamine-hydrolyzing) activity
Specific function:
Catalyzes the synthesis of GMP from XMP
Gene Name:
guaA
Locus Tag:
PA3769
Molecular weight:
58 kDa
Reactions
ATP + xanthosine 5'-phosphate + L-glutamine + H(2)O = AMP + diphosphate + GMP + L-glutamate.
General function:
Involved in biosynthetic process
Specific function:
Catalyzes the biosynthesis of 4-amino-4-deoxychorismate (ADC) from chorismate and glutamine
Gene Name:
pabB
Locus Tag:
PA1758
Molecular weight:
49.6 kDa
Reactions
Chorismate + L-glutamine = 4-amino-4-deoxychorismate + L-glutamate.
General function:
Involved in catalytic activity
Specific function:
2 L-glutamate + NADP(+) = L-glutamine + 2- oxoglutarate + NADPH
Gene Name:
gltB
Locus Tag:
PA5036
Molecular weight:
161.6 kDa
Reactions
2 L-glutamate + NADP(+) = L-glutamine + 2-oxoglutarate + NADPH.
General function:
Involved in iron-sulfur cluster binding
Specific function:
2 L-glutamate + NADP(+) = L-glutamine + 2- oxoglutarate + NADPH
Gene Name:
gltD
Locus Tag:
PA5035
Molecular weight:
52.6 kDa
Reactions
2 L-glutamate + NADP(+) = L-glutamine + 2-oxoglutarate + NADPH.
General function:
Involved in glutamine catabolic process
Specific function:
2 ATP + L-glutamine + HCO(3)(-) + H(2)O = 2 ADP + phosphate + L-glutamate + carbamoyl phosphate
Gene Name:
carA
Locus Tag:
PA4758
Molecular weight:
40.8 kDa
Reactions
2 ATP + L-glutamine + HCO(3)(-) + H(2)O = 2 ADP + phosphate + L-glutamate + carbamoyl phosphate.
General function:
Involved in glutaminase activity
Specific function:
L-glutamine + H(2)O = L-glutamate + NH(3)
Gene Name:
glsA2
Locus Tag:
PA1638
Molecular weight:
33 kDa
Reactions
L-glutamine + H(2)O = L-glutamate + NH(3).
General function:
Involved in CTP synthase activity
Specific function:
Catalyzes the ATP-dependent amination of UTP to CTP with either L-glutamine or ammonia as the source of nitrogen
Gene Name:
pyrG
Locus Tag:
PA3637
Molecular weight:
59.6 kDa
Reactions
ATP + UTP + NH(3) = ADP + phosphate + CTP.
General function:
Involved in glutamate-ammonia ligase activity
Specific function:
ATP + L-glutamate + NH(3) = ADP + phosphate + L-glutamine
Gene Name:
glnA
Locus Tag:
PA5119
Molecular weight:
51.9 kDa
Reactions
ATP + L-glutamate + NH(3) = ADP + phosphate + L-glutamine.
General function:
Involved in amidophosphoribosyltransferase activity
Specific function:
5-phospho-beta-D-ribosylamine + diphosphate + L-glutamate = L-glutamine + 5-phospho-alpha-D-ribose 1-diphosphate + H(2)O
Gene Name:
purF
Locus Tag:
PA3108
Molecular weight:
55.4 kDa
Reactions
5-phospho-beta-D-ribosylamine + diphosphate + L-glutamate = L-glutamine + 5-phospho-alpha-D-ribose 1-diphosphate + H(2)O.
General function:
Involved in catalytic activity
Specific function:
ATP + N(2)-formyl-N(1)-(5-phospho-D- ribosyl)glycinamide + L-glutamine + H(2)O = ADP + phosphate + 2- (formamido)-N(1)-(5-phospho-D-ribosyl)acetamidine + L-glutamate
Gene Name:
purL
Locus Tag:
PA3763
Molecular weight:
140.6 kDa
Reactions
ATP + N(2)-formyl-N(1)-(5-phospho-D-ribosyl)glycinamide + L-glutamine + H(2)O = ADP + phosphate + 2-(formamido)-N(1)-(5-phospho-D-ribosyl)acetamidine + L-glutamate.
General function:
Involved in metabolic process
Specific function:
Catalyzes the first step in hexosamine metabolism, converting fructose-6P into glucosamine-6P using glutamine as a nitrogen source
Gene Name:
glmS
Locus Tag:
PA5549
Molecular weight:
66.3 kDa
Reactions
L-glutamine + D-fructose 6-phosphate = L-glutamate + D-glucosamine 6-phosphate.
General function:
Involved in NAD+ synthase (glutamine-hydrolyzing) activity
Specific function:
Catalyzes a key step in NAD biosynthesis, transforming deamido-NAD into NAD by a two-step reaction
Gene Name:
nadE
Locus Tag:
PA4920
Molecular weight:
29.7 kDa
Reactions
ATP + deamido-NAD(+) + NH(3) = AMP + diphosphate + NAD(+).

Transporters

General function:
Involved in nucleotide binding
Specific function:
Probably part of a binding-protein-dependent transport system yecCS for an amino acid. Probably responsible for energy coupling to the transport system
Gene Name:
yecC
Locus Tag:
PA5152
Molecular weight:
28.4 kDa