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L-gamma-Glutamyl-L-alanine (YMDB00691)

Identification
YMDB IDYMDB00691
NameL-gamma-Glutamyl-L-alanine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptiongamma-Glutamylalanine, also known as 5-L-glutamyl-L-alanine or L-gamma-glu-L-ala, belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. gamma-Glutamylalanine exists in all eukaryotes, ranging from yeast to plants to humans. Based on a literature review a significant number of articles have been published on gamma-Glutamylalanine.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
  • (5-L-Glutamyl)-L-amino acid
  • 5-L-glutamylalanine
  • g-Glu-Ala
  • g-Glutamylalanine
  • g-L-Glutamyl-L-alanine
  • gamma-Gln-Ala
  • gamma-Glu-Ala
  • gamma-Glutamylalanine
  • gamma-L-Glutamyl-L-alanine
  • L-gamma-Glutamyl-L-amino acid
  • N-L-gamma-glutamyl-L-alanine
  • 5-L-Glutamyl-L-alanine
  • L-gamma-Glu-L-ala
  • Γ-L-glutamyl-L-alanine
  • L-g-Glu-L-ala
  • L-Γ-glu-L-ala
  • N-L-g-Glutamyl-L-alanine
  • N-L-Γ-glutamyl-L-alanine
  • Γ-glutamylalanine
  • γ-Glu-Ala
  • γ-L-Glu-L-Ala
  • L-γ-Glutamyl-L-alanine
  • N-γ-Glutamylalanine
  • N-L-γ-Glutamylalanine
  • gamma-L-Glu-L-Ala
  • L-gamma-Glutamyl-L-alanine
  • N-gamma-Glutamylalanine
  • N-L-gamma-Glutamylalanine
  • N-γ-L-Glutamyl-L-alanine
  • N-gamma-L-Glutamyl-L-alanine
CAS number5875-41-2
WeightAverage: 218.2072
Monoisotopic: 218.090271568
InChI KeyWQXXXVRAFAKQJM-WHFBIAKZSA-N
InChIInChI=1S/C8H14N2O5/c1-4(7(12)13)10-6(11)3-2-5(9)8(14)15/h4-5H,2-3,9H2,1H3,(H,10,11)(H,12,13)(H,14,15)/t4-,5-/m0/s1
IUPAC Name(2S)-2-amino-4-{[(1S)-1-carboxyethyl]carbamoyl}butanoic acid
Traditional IUPAC Nameg-glu-ala
Chemical FormulaC8H14N2O5
SMILESC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • Gamma-glutamyl alpha-amino acid
  • Glutamine or derivatives
  • N-acyl-l-alpha-amino acid
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alanine or derivatives
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Dicarboxylic acid or derivatives
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Fatty acid
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic oxygen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Amine
  • Primary amine
  • Organonitrogen compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility12.9 g/LALOGPS
logP-3.4ALOGPS
logP-3.8ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)1.93ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area129.72 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity48.59 m³·mol⁻¹ChemAxon
Polarizability20.94 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Glutathione metabolismPW002395 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glutathione metabolismec00480 Map00480
SMPDB ReactionsNot Available
KEGG Reactions
Glutathione + L-Alanine → L-cysteinylglycine + L-gamma-Glutamyl-L-alanine
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00al-9710000000-e2845b73a5e7cd81881fJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dj-9332000000-f7980440d2535885b7abJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00xr-2940000000-948d6e9385d802328937JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05br-6900000000-5f1480e854581ee71678JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-9200000000-58a633696455e707016dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0690000000-92c8a111979eb46fa59fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06dj-2930000000-1156c919eda2b8e49faeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0076-9200000000-737e76bca1d968721a2aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000x-9330000000-8674f1f30751437e8bf9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9300000000-a9c7516230cc6b7166c1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053u-9100000000-bb369086fe31b624af6cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-056r-1900000000-491b535e4d4e3214438cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9100000000-51f9fd3eeccf33a98c1cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-9000000000-d6a5f92f606e802c70beJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID50619
HMDB IDHMDB06248
Pubchem Compound ID440103
Kegg IDC03740
ChemSpider ID389104
FOODB IDFDB023860
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Gamma-glutamyltransferase
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Plays a role in the turnover of the vacuolar glutathione and in the supply of growth requirements during nitrogen starvation
Gene Name:
ECM38
Uniprot ID:
Q05902
Molecular weight:
73179.79688
Reactions
(5-L-glutamyl)-peptide + an amino acid → peptide + 5-L-glutamyl amino acid.