Record Information
Version2.0
Creation Date2012-05-31 10:22:23 -0600
Update Date2015-09-13 12:56:06 -0600
Secondary Accession Numbers
  • ECMDB00161
Identification
Name:L-Alanine
DescriptionAlanine is an amino acid made from the conversion of the carbohydrate pyruvate or the breakdown of DNA and the dipeptides carnosine and anserine. Alanine is an important participant as well as regulator in glucose metabolism. Normal alanine metabolism, like that of other amino acids, is highly dependent upon enzymes that contain vitamin B6. (http://www.dcnutrition.com/AminoAcids/)
Structure
Thumb
Synonyms:
  • (2S)-2-Aminopropanoate
  • (2S)-2-Aminopropanoic acid
  • (S)-(+)-Alanine
  • (S)-2-amino-Propanoate
  • (S)-2-amino-Propanoic acid
  • (S)-2-Aminopropanoate
  • (S)-2-Aminopropanoic acid
  • (S)-Alanine
  • 2-Aminopropanoate
  • 2-Aminopropanoic acid
  • 2-Aminopropionate
  • 2-Aminopropionic acid
  • 2-Ammoniopropanoate
  • 2-Ammoniopropanoic acid
  • A
  • A-Alanine
  • a-Aminopropanoate
  • a-Aminopropanoic acid
  • A-Aminopropionate
  • A-Aminopropionic acid
  • Ala
  • Alanine
  • Alpha-Alanine
  • Alpha-Aminopropanoate
  • Alpha-Aminopropanoic acid
  • Alpha-Aminopropionate
  • Alpha-Aminopropionic acid
  • L-α-alanine
  • L-(+)-Alanine
  • L-2-Aminopropanoate
  • L-2-Aminopropanoic acid
  • L-2-Aminopropionate
  • L-2-Aminopropionic acid
  • L-a-Alanine
  • L-a-Aminopropionate
  • L-a-Aminopropionic acid
  • L-alpha-Alanine
  • L-alpha-Aminopropionate
  • L-alpha-Aminopropionic acid
  • L-α-Alanine
  • L-α-Aminopropionate
  • L-α-Aminopropionic acid
  • α-Alanine
  • α-Aminopropanoate
  • α-Aminopropanoic acid
  • α-Aminopropionate
  • α-Aminopropionic acid
Chemical Formula:C3H7NO2
Weight:Average: 89.0932
Monoisotopic: 89.047678473
InChI Key:QNAYBMKLOCPYGJ-REOHCLBHSA-N
InChI:InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m0/s1
CAS number:56-41-7
IUPAC Name:(2S)-2-aminopropanoic acid
Traditional IUPAC Name:L-alanine
SMILES:C[C@H](N)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as alanine and derivatives. Alanine and derivatives are compounds containing alanine or a derivative thereof resulting from reaction of alanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlanine and derivatives
Alternative Parents
Substituents
  • Alanine or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Organopnictogen compound
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:300 °C
Experimental Properties:
PropertyValueSource
Water Solubility:164.0 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; 204 mg/mL [HMP experimental]PhysProp
LogP:-2.85 [SANGSTER (1994)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility447 g/LALOGPS
logP-3ALOGPS
logP-2.8ChemAxon
logS0.7ALOGPS
pKa (Strongest Acidic)2.47ChemAxon
pKa (Strongest Basic)9.48ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity20.5 m³·mol⁻¹ChemAxon
Polarizability8.49 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
L-Alanine + Pyridoxal 5'-phosphate > Pyridoxamine 5'-phosphate + Pyruvic acid
L-Alanine <> D-Alanine
L-Cysteine + SufSE sulfur acceptor complex > L-Alanine + SufSE with bound sulfur
alpha-Ketoglutarate + L-Alanine <> L-Glutamate + Pyruvic acid
Adenosine triphosphate + Water + L-Alanine > ADP + L-Alanine + Hydrogen ion + Phosphate
Adenosine triphosphate + Water + L-Alanine > ADP + L-Alanine + Hydrogen ion + Phosphate
L-Alanine + Adenosine triphosphate + UDP-N-Acetylmuraminate <> ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanine
L-Alanine-L-glutamate + Water > L-Alanine + L-Glutamate
L-Alanine + Pimeloyl-[acyl-carrier protein] > 8-Amino-7-oxononanoate + acyl carrier protein + Carbon dioxide
L-Cysteine + IscS sulfur acceptor protein > L-Alanine + IscS with bound sulfur
L-Alanine + Adenosine triphosphate + tRNA(Ala) > L-Alanyl-tRNA(Ala) + Adenosine monophosphate + Pyrophosphate
3-Sulfinoalanine + 2 Hydrogen ion > L-Alanine + Sulfur dioxide
alpha-Ketoisovaleric acid + L-Alanine <> Pyruvic acid + L-Valine + a-Ketoisovaleric acid
L-Valine + Pyruvic acid <> alpha-Ketoisovaleric acid + L-Alanine
Adenosine triphosphate + L-Alanine + tRNA(Ala) + tRNA(Ala) <> Adenosine monophosphate + Pyrophosphate + L-Alanyl-tRNA + L-Alanyl-tRNA
Adenosine triphosphate + UDP-N-Acetylmuraminate + L-Alanine <> ADP + Phosphate + UDP-N-Acetylmuramoyl-L-alanine
6-Carboxyhexanoyl-CoA + L-Alanine + Pimeloyl-[acyl-carrier protein] <> 8-Amino-7-oxononanoate + Coenzyme A + Carbon dioxide + Acyl-carrier protein
Selenocysteine + Reduced acceptor <> Hydrogen selenide + L-Alanine + Acceptor
N-Acetylmuramoyl-Ala + Water <> N-Acetyl-D-muramoate + L-Alanine
[Enzyme]-cysteine + L-Cysteine <> [Enzyme]-S-sulfanylcysteine + L-Alanine
UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate-D-alanine + Water > L-Alanine + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate
Hydrogen ion + L-Alanine + pimeloyl-CoA > Carbon dioxide + Coenzyme A + 8-Amino-7-oxononanoate
Oxoglutaric acid + L-Alanine <> L-Glutamate + Pyruvic acid
L-Alanine + Hydrogen ion + Pimeloyl-ACPs > 8-Amino-7-oxononanoate + Carbon dioxide + ACP
L-Cysteine + a sulfur acceptor + Hydrogen ion L-Alanine + <i>S</i>-sulfanyl-[acceptor]
3-Sulfinoalanine + Water Hydrogen ion + L-Alanine + Sulfite
L-Cysteine + L-Cysteine-Desulfurases > L-Alanine + Persulfurated-L-cysteine-desulfurases
ala-asp + Water > L-Alanine + L-Aspartic acid
ala-gln + Water > L-Alanine + L-Glutamine
ala-gly + Water > L-Alanine + Glycine
ala-his + Water > L-Alanine + L-Histidine
ala-leu + Water > L-Alanine + L-Leucine
ala-thr + Water > L-Alanine + L-Threonine
L-Alanyl-L-Glutamate + Water > L-Alanine + L-Glutamate
methionine-alanine dipeptide + Water > L-Methionine + L-Alanine
a reduced electron acceptor + Selenocysteine <> L-Alanine + Selenium + an oxidized electron acceptor + Hydrogen ion
L-Alanine + Oxoglutaric acid > Pyruvic acid + L-Glutamate
L-Alanine > D-Alanine
L-Valine + Pyruvic acid > a-Ketoisovaleric acid + L-Alanine
6-carboxyhexanoyl-CoA + L-Alanine > 8-Amino-7-oxononanoate + CoA + Carbon dioxide
L-Cysteine + acceptor > L-Alanine + S-sulfanyl-acceptor
Adenosine triphosphate + UDP-N-Acetylmuraminate + L-Alanine > ADP + Inorganic phosphate + UDP-N-Acetylmuramoyl-L-alanine
Selenocysteine + reduced acceptor > Hydrogen selenide + L-Alanine + acceptor
a pimeloyl-[acp] + L-Alanine + L-Alanine > Carbon dioxide + a holo-[acyl-carrier protein] + 8-Amino-7-oxononanoate
a sulfurated [sulfur carrier] + L-Alanine + L-Alanine > 8-Amino-7-oxononanoate + Coenzyme A + Carbon dioxide
L-Alanine + L-Alanine <> D-Alanine
L-Alanine + L-Alanine > D-Alanine
UDP-N-acetylmuraminate + Adenosine triphosphate + L-Alanine + UDP-N-Acetylmuraminate + L-Alanine > UDP-N-Acetylmuramoyl-L-alanine + Adenosine diphosphate + Phosphate + ADP
Adenosine triphosphate + L-Alanine + tRNA(Ala) + L-Alanine > Adenosine monophosphate + Pyrophosphate + L-alanyl-tRNA(Ala)
L-Alanine + Oxoglutaric acid + L-Alanine <> L-Glutamic acid + Pyruvic acid + L-Glutamate
L-Alanine + Glyoxylic acid + L-Alanine <> Glycine + Pyruvic acid
Pyruvic acid + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + L-Alanine + L-Alanine
L-Cysteine + an [L-cysteine desulfurase] L-cysteine persulfide > an [L-cysteine desulfurase] L-cysteine persulfide + L-Alanine + L-Alanine
L-Valine + Pyruvic acid + L-Valine > L-Alanine + a-Ketoisovaleric acid + L-Alanine
L-Alanine + Adenosine triphosphate + Hydrogen ion + tRNA(Ala) + L-Alanine > Pyrophosphate + Adenosine monophosphate + L-alanyl-tRNA(Ala)
UDP-N-acetyl-α-D-muramate + L-Alanine + Adenosine triphosphate + L-Alanine > Adenosine diphosphate + Phosphate + Hydrogen ion + UDP-N-Acetylmuramoyl-L-alanine + ADP
UDP-N-acetyl-α-D-muramate + Adenosine triphosphate + L-Alanine > UDP-N-Acetylmuramyl-L-Ala + ADP + Phosphate + Hydrogen ion
6 6-carboxyhexanoyl-CoA + L-Alanine + Pimeloyl-[acyl-carrier protein] <>8 8-Amino-7-oxononanoate + Coenzyme A + Carbon dioxide + Acyl-carrier protein
Adenosine triphosphate + L-Alanine + tRNA(Ala) <> Adenosine monophosphate + Pyrophosphate + L-Alanyl-tRNA
alpha-Ketoglutarate + L-Alanine <> L-Glutamate + Pyruvic acid
N-Acetylmuramoyl-Ala + Water <> N-Acetyl-D-muramoate + L-Alanine
[Enzyme]-cysteine + L-Cysteine <> [Enzyme]-S-sulfanylcysteine + L-Alanine
L-Alanine + Adenosine triphosphate + UDP-N-Acetylmuraminate <> ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanine
L-Alanine <> D-Alanine
Adenosine triphosphate + L-Alanine + tRNA(Ala) <> Adenosine monophosphate + Pyrophosphate + L-Alanyl-tRNA
alpha-Ketoglutarate + L-Alanine <> L-Glutamate + Pyruvic acid
N-Acetylmuramoyl-Ala + Water <> N-Acetyl-D-muramoate + L-Alanine
[Enzyme]-cysteine + L-Cysteine <> [Enzyme]-S-sulfanylcysteine + L-Alanine
L-Alanine + Adenosine triphosphate + UDP-N-Acetylmuraminate <> ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanine
alpha-Ketoglutarate + L-Alanine <> L-Glutamate + Pyruvic acid
L-Alanine <> D-Alanine
More...

SMPDB Pathways:
Biotin metabolismPW000762 ThumbThumb?image type=greyscaleThumb?image type=simple
D-Alanine metabolismPW000768 ThumbThumb?image type=greyscaleThumb?image type=simple
D-Glutamine and D-glutamate metabolismPW000769 ThumbThumb?image type=greyscaleThumb?image type=simple
L-alanine metabolismPW000788 ThumbThumb?image type=greyscaleThumb?image type=simple
inner membrane transportPW000786 ThumbThumb?image type=greyscaleThumb?image type=simple
peptidoglycan biosynthesis IPW000906 ThumbThumb?image type=greyscaleThumb?image type=simple
peptidoglycan biosynthesis I 2PW002062 ThumbThumb?image type=greyscaleThumb?image type=simple
tRNA Charging 2PW000803 ThumbThumb?image type=greyscaleThumb?image type=simple
tRNA chargingPW000799 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
2550± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucoseMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
1770± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerolMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
879± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetateMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
358± 0 uMBW2511348 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L GlucoStationary Phase, glucose limitedBioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h37 oCPMID: 17379776
832± 67 uMBL21 DE3Luria-Bertani (LB) mediaStationary phase cultures (overnight culture)Shake flask37 oCExperimentally Determined
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915± 44 uMBL21 DE3Luria-Bertani (LB) mediaStationary phase cultures (overnight culture)Shake flask37 oCExperimentally Determined
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Find out more about how we convert literature concentrations.
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-014i-0900000000-c7f6dbace291e8305a4eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-014i-0900000000-381ddf4d9ea77be0b8a5View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-01b9-6900000000-6a7c1bb2915e5dd0791fView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-014i-1900000000-84b389f82562c29a8148View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kf-9000000000-b2f7507be509a85d821bView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-0900000000-941672891ab94cf5015dView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f79-0910000000-47bd3e3aa274a653a64eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0900000000-c7f6dbace291e8305a4eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0900000000-381ddf4d9ea77be0b8a5View in MoNA
GC-MSGC-MS Spectrum - GC-EI-QQ (Non-derivatized)splash10-0a4i-1940000000-5def9f7c902aaf1ef607View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01b9-6900000000-6a7c1bb2915e5dd0791fView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-1900000000-84b389f82562c29a8148View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-d31f7a2ed8284a740b59View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-9100000000-ab365202f52df8e6d401View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-9000000000-96b54b269c91ab21be08View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-a8008305399aa1097e1aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-7253c912562200edc231View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-00kf-9000000000-72694f3a1a5de3b49790View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-9000000000-55d0139f513946f76461View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9000000000-5b0dff13a98daf782205View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9000000000-37db595fcf7364600bc9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0006-9000000000-5129e160acf979ac549eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0006-9000000000-11c20eba8c5ad41d806cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0006-9000000000-df7c7d6a6ae2d6bccefeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0006-9000000000-32477244247613182214View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-000f-9002000000-4873ce0cdcac54d68186View in MoNA
LC-MS/MSLC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positivesplash10-0006-9000000000-8193842b36c819ca3ec6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-55d0139f513946f76461View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-5b0dff13a98daf782205View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-37db595fcf7364600bc9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-fefc31c264a2f0fcf6d0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-ba42bcd60aa9182a780eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-df7c7d6a6ae2d6bccefeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-080ffbbf05d95b7bcfe6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-0dfcc5cb0b7d9f01e04aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002f-9000000000-130c999fe6b63419cfa1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-2ddc0bb04bae8f928a23View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-98c403c9cd494594babfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-38a12affa4e4f4e91626View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
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  • Saklatvala J: Hydrolysis of the elastase substrate succinyltrialanine nitroanilide by a metal-dependent enzyme in rheumatoid synovial fluid. J Clin Invest. 1977 May;59(5):794-801. Pubmed: 16038
  • 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
  • Stahl A, Frick A, Imler M, Schlienger JL: Semiautomated enzymic microassay for plasma L-alanine. Enzyme. 1979;24(5):294-301. Pubmed: 41707
  • 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
  • Wevers RA, Engelke U, Wendel U, de Jong JG, Gabreels FJ, Heerschap A: Standardized method for high-resolution 1H-NMR of cerebrospinal fluid. Clin Chem. 1995 May;41(5):744-51. Pubmed: 7729054
  • 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:Chibata I; Kakimoto T; Kato J Enzymatic production of L-alanine by Pseudomonas dacunhae. Applied microbiology (1965), 13(5), 638-45.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID16977
HMDB IDHMDB00161
Pubchem Compound ID5950
Kegg IDC00041
ChemSpider ID5735
WikipediaAlanine
BioCyc IDL-ALPHA-ALANINE
EcoCyc IDL-ALPHA-ALANINE
Ligand ExpoALA_LFZW

Enzymes

General function:
Involved in nucleotide binding
Specific function:
Edits incorrectly charged Ser-tRNA(Ala) and Gly- tRNA(Ala) but not incorrectly charged Ser-tRNA(Thr)
Gene Name:
alaS
Uniprot ID:
P00957
Molecular weight:
96032
Reactions
ATP + L-alanine + tRNA(Ala) = AMP + diphosphate + L-alanyl-tRNA(Ala).
General function:
Involved in transferase activity
Specific function:
L-valine + pyruvate = 3-methyl-2-oxobutanoate + L-alanine
Gene Name:
avtA
Uniprot ID:
P09053
Molecular weight:
46711
Reactions
L-valine + pyruvate = 3-methyl-2-oxobutanoate + L-alanine.
General function:
Involved in alanine racemase activity
Specific function:
Provides the D-alanine required for cell wall biosynthesis
Gene Name:
alr
Uniprot ID:
P0A6B4
Molecular weight:
39153
Reactions
L-alanine = D-alanine.
General function:
Involved in metabolic process
Specific function:
Catalyzes the removal of elemental sulfur and selenium atoms from cysteine and selenocysteine to produce alanine. Functions as a sulfur delivery protein for NAD, biotin and Fe-S cluster synthesis. Transfers sulfur on 'Cys-456' of thiI in a transpersulfidation reaction. Transfers sulfur on 'Cys-19' of tusA in a transpersulfidation reaction. Functions also as a selenium delivery protein in the pathway for the biosynthesis of selenophosphate
Gene Name:
iscS
Uniprot ID:
P0A6B7
Molecular weight:
45089
Reactions
L-cysteine + acceptor = L-alanine + S-sulfanyl-acceptor.
General function:
Involved in catalytic activity
Specific function:
Interconversion of serine and glycine
Gene Name:
glyA
Uniprot ID:
P0A825
Molecular weight:
45316
Reactions
5,10-methylenetetrahydrofolate + glycine + H(2)O = tetrahydrofolate + L-serine.
General function:
Involved in 8-amino-7-oxononanoate synthase activity
Specific function:
Catalyzes the decarboxylative condensation of pimeloyl- CoA and L-alanine to produce 8-amino-7-oxononanoate (AON), coenzyme A, and carbon dioxide
Gene Name:
bioF
Uniprot ID:
P12998
Molecular weight:
41594
Reactions
6-carboxyhexanoyl-CoA + L-alanine = 8-amino-7-oxononanoate + CoA + CO(2).
General function:
Involved in hydrolase activity
Specific function:
Dipeptidase with broad substrate specificity. Requires dipeptide substrates with an unblocked N-terminus and the amino group in the alpha or beta position. Non-protein amino acids and proline are not accepted in the C-terminal position, whereas some dipeptide amides and formyl amino acids are hydrolyzed. Also shows cysteinylglycinase activity, which is sufficient for E.coli to utilize cysteinylglycine as a cysteine source
Gene Name:
pepD
Uniprot ID:
P15288
Molecular weight:
52915
Reactions
Hydrolysis of dipeptides, preferentially hydrophobic dipeptides including prolyl amino acids.
General function:
Involved in ATP binding
Specific function:
Cell wall formation
Gene Name:
murC
Uniprot ID:
P17952
Molecular weight:
53626
Reactions
ATP + UDP-N-acetylmuramate + L-alanine = ADP + phosphate + UDP-N-acetylmuramoyl-L-alanine.
General function:
Involved in N-acetylmuramoyl-L-alanine amidase activity
Specific function:
Cell-wall hydrolase probably involved in cell-wall hydrolysis, septation or recycling
Gene Name:
amiB
Uniprot ID:
P26365
Molecular weight:
47985
Reactions
Hydrolyzes the link between N-acetylmuramoyl residues and L-amino acid residues in certain cell-wall glycopeptides.
General function:
Involved in alanine racemase activity
Specific function:
Isomerizes L-alanine to D-alanine which is then oxidized to pyruvate by dadA
Gene Name:
dadX
Uniprot ID:
P29012
Molecular weight:
38844
Reactions
L-alanine = D-alanine.
General function:
Involved in N-acetylmuramoyl-L-alanine amidase activity
Specific function:
Hydrolyzes the link between N-acetylmuramoyl residues and L-amino acid residues in certain cell-wall glycopeptides
Gene Name:
amiA
Uniprot ID:
P36548
Molecular weight:
31412
Reactions
Hydrolyzes the link between N-acetylmuramoyl residues and L-amino acid residues in certain cell-wall glycopeptides.
General function:
Involved in N-acetylmuramoyl-L-alanine amidase activity
Specific function:
Cell-wall hydrolase probably involved in cell-wall hydrolysis, septation or recycling
Gene Name:
amiC
Uniprot ID:
P63883
Molecular weight:
45634
Reactions
Hydrolyzes the link between N-acetylmuramoyl residues and L-amino acid residues in certain cell-wall glycopeptides.
General function:
Involved in lyase activity
Specific function:
Catalyzes the cleavage of L-allo-threonine and L- threonine to glycine and acetaldehyde. L-threo-phenylserine and L- erythro-phenylserine are also good substrates
Gene Name:
ltaE
Uniprot ID:
P75823
Molecular weight:
36494
Reactions
L-threonine = glycine + acetaldehyde.
L-allo-threonine = glycine + acetaldehyde.
General function:
Defense mechanisms
Specific function:
Releases the terminal D-alanine residue from the cytoplasmic tetrapeptide recycling product L-Ala-gamma-D-Glu-meso- Dap-D-Ala. To a lesser extent, can also cleave D-Ala from murein derivatives containing the tetrapeptide, i.e. MurNAc-tetrapeptide, UDP-MurNAc-tetrapeptide, GlcNAc-MurNAc-tetrapeptide, and GlcNAc- anhMurNAc-tetrapeptide. Does not act on murein sacculi or cross- linked muropeptides. The tripeptides produced by the lcdA reaction can then be reused as peptidoglycan building blocks; lcdA is thereby involved in murein recycling. Is also essential for viability during stationary phase
Gene Name:
ldcA
Uniprot ID:
P76008
Molecular weight:
33567
Reactions
GlcNAc-MurNAc-L-alanyl-gamma-D-glutamyl-meso-diaminopimelyl-D-alanine + H(2)O = GlcNAc-MurNAc-L-alanyl-gamma-D-glutamyl-meso-diaminopimelate + D-alanine.
General function:
Involved in metabolic process
Specific function:
Cysteine desulfurases mobilize the sulfur from L- cysteine to yield L-alanine, an essential step in sulfur metabolism for biosynthesis of a variety of sulfur-containing biomolecules. Component of the suf operon, which is activated and required under specific conditions such as oxidative stress and iron limitation. Acts as a potent selenocysteine lyase in vitro, that mobilizes selenium from L-selenocysteine. Selenocysteine lyase activity is however unsure in vivo
Gene Name:
sufS
Uniprot ID:
P77444
Molecular weight:
44433
Reactions
L-cysteine + acceptor = L-alanine + S-sulfanyl-acceptor.
L-selenocysteine + reduced acceptor = selenide + L-alanine + acceptor.
General function:
Involved in metabolic process
Specific function:
Catalyzes the removal of elemental sulfur and selenium atoms from L-cysteine, L-cystine, L-selenocysteine, and L- selenocystine to produce L-alanine. L-cysteine sulfinic acid is the best substrate. Functions as a selenium delivery protein in the pathway for the biosynthesis of selenophosphate
Gene Name:
csdA
Uniprot ID:
Q46925
Molecular weight:
43234
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for branched-chain amino acids. Probably responsible for the translocation of the substrates across the membrane
Gene Name:
livH
Uniprot ID:
P0AEX7
Molecular weight:
32982
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for branched-chain amino acids. Probably responsible for the translocation of the substrates across the membrane
Gene Name:
livM
Uniprot ID:
P22729
Molecular weight:
46269
General function:
Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:
Specific function unknown
Gene Name:
yfbQ
Uniprot ID:
P0A959
Molecular weight:
45517
Reactions
L-alanine + 2-oxoglutarate = pyruvate + L-glutamate.
General function:
Not Available
Specific function:
Participates in cysteine desulfuration mediated by sufS. Cysteine desulfuration mobilizes sulfur from L-cysteine to yield L-alanine and constitutes an essential step in sulfur metabolism for biosynthesis of a variety of sulfur-containing biomolecules. Functions as a sulfur acceptor for sufS, by mediating the direct transfer of the sulfur atom from the S-sulfanylcysteine of sufS, an intermediate product of cysteine desulfuration process. Together with the sufBCD complex, it thereby enhances up to 50- fold, the cysteine desulfurase activity of sufS. Component of the suf operon, which is activated and required under specific conditions such as oxidative stress and iron limitation. Does not affect the selenocysteine lyase activity of sufS
Gene Name:
sufE
Uniprot ID:
P76194
Molecular weight:
15800
General function:
Involved in nucleotide binding
Specific function:
Component of the leucine-specific transport system
Gene Name:
livG
Uniprot ID:
P0A9S7
Molecular weight:
28427
General function:
Involved in amino acid transport
Specific function:
This protein is a component of the leucine, isoleucine, valine, (threonine) transport system, which is one of the two periplasmic binding protein-dependent transport systems of the high-affinity transport of the branched-chain amino acids
Gene Name:
livJ
Uniprot ID:
P0AD96
Molecular weight:
39076
General function:
Involved in nucleotide binding
Specific function:
Component of the leucine-specific transport system
Gene Name:
livF
Uniprot ID:
P22731
Molecular weight:
26310
General function:
Amino acid transport and metabolism
Specific function:
Specific function unknown
Gene Name:
yfdZ
Uniprot ID:
P77434
Molecular weight:
46216
Reactions
L-alanine + 2-oxoglutarate = pyruvate + L-glutamate.

Transporters

General function:
Involved in sodium:amino acid symporter activity
Specific function:
Specific function unknown
Gene Name:
yaaJ
Uniprot ID:
P30143
Molecular weight:
51662
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
Uniprot ID:
P37774
Molecular weight:
27677
General function:
Involved in transporter activity
Specific function:
Probably part of the binding-protein-dependent transport system yecCS for an amino acid; probably responsible for the translocation of the substrate across the membrane
Gene Name:
yecS
Uniprot ID:
P0AFT2
Molecular weight:
24801
General function:
Involved in transport
Specific function:
Permease that is involved in the transport across the cytoplasmic membrane of D-alanine, D-serine and glycine
Gene Name:
cycA
Uniprot ID:
P0AAE0
Molecular weight:
51659
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for branched-chain amino acids. Probably responsible for the translocation of the substrates across the membrane
Gene Name:
livH
Uniprot ID:
P0AEX7
Molecular weight:
32982
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for branched-chain amino acids. Probably responsible for the translocation of the substrates across the membrane
Gene Name:
livM
Uniprot ID:
P22729
Molecular weight:
46269
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in nucleotide binding
Specific function:
Component of the leucine-specific transport system
Gene Name:
livG
Uniprot ID:
P0A9S7
Molecular weight:
28427
General function:
Involved in amino acid transport
Specific function:
This protein is a component of the leucine, isoleucine, valine, (threonine) transport system, which is one of the two periplasmic binding protein-dependent transport systems of the high-affinity transport of the branched-chain amino acids
Gene Name:
livJ
Uniprot ID:
P0AD96
Molecular weight:
39076
General function:
Involved in nucleotide binding
Specific function:
Component of the leucine-specific transport system
Gene Name:
livF
Uniprot ID:
P22731
Molecular weight:
26310
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368