Identification |
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YMDB ID | YMDB00252 |
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Name | Gamma-Glutamylcysteine |
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Species | Saccharomyces cerevisiae |
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Strain | Baker's yeast |
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Description | gamma-Glutamylcysteine, also known as L-γ-glutamylcysteine or gamma-glu-cys, belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. gamma-Glutamylcysteine is a very strong basic compound (based on its pKa). gamma-Glutamylcysteine exists in all living species, ranging from bacteria to humans. gamma-Glutamylcysteine is a potentially toxic compound. |
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Structure | |
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Synonyms | - (Des-Gly)-Glutathione
- 3GC
- 5-L-Glutamyl-L-cysteine
- 5-L-glutamylcysteine
- g-Glutamylcysteine
- g-L-Glutamyl-L-cysteine
- gamma-Glu-cys
- gamma-Glutamylcysteine
- gamma-L-Glutamyl-L-cysteine
- H-gamma-Glu-Cys-OH
- H-Glu(Cys-OH)-OH
- L-g-Glutamyl-L-cysteine
- L-gamma-Glutamyl-L-cysteine
- L-gamma-Glutamylcysteine
- N-(1-carboxy-2-mercaptoethyl)-L-Glutamine
- N-L-gamma-glutamyl-L-Cysteine
- xN-L-g-glutamyl-Glutamine
- xN-L-gamma-glutamyl-Glutamine
- g-Glu-cys
- Γ-glu-cys
- Γ-L-glutamyl-L-cysteine
- L-g-Glutamylcysteine
- L-Γ-glutamylcysteine
- Γ-glutamylcysteine
- Γ-L-glu-L-cys
- L-Γ-glutamyl-L-cysteine
- N-Γ-glutamylcysteine
- N-L-Γ-glutamylcysteine
- N-L-Γ-glutamyl-L-cysteine
- gamma-L-Glu-L-cys
- N-gamma-Glutamylcysteine
- N-L-gamma-Glutamylcysteine
- N-Γ-L-glutamyl-L-cysteine
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CAS number | 636-58-8 |
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Weight | Average: 250.272 Monoisotopic: 250.062342258 |
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InChI Key | RITKHVBHSGLULN-WHFBIAKZSA-N |
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InChI | InChI=1S/C8H14N2O5S/c9-4(7(12)13)1-2-6(11)10-5(3-16)8(14)15/h4-5,16H,1-3,9H2,(H,10,11)(H,12,13)(H,14,15)/t4-,5-/m0/s1 |
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IUPAC Name | (2S)-2-amino-4-{[(1R)-1-carboxy-2-sulfanylethyl]carbamoyl}butanoic acid |
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Traditional IUPAC Name | gamma-glutamylcysteine |
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Chemical Formula | C8H14N2O5S |
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SMILES | [H]OC(=O)[C@@]([H])(N([H])[H])C([H])([H])C([H])([H])C(=O)N([H])[C@]([H])(C(=O)O[H])C([H])([H])S[H] |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | N-acyl-alpha amino acids |
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Alternative Parents | |
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Substituents | - N-acyl-alpha-amino acid
- Cysteine or derivatives
- Alpha-amino acid
- L-alpha-amino acid
- Fatty acid
- Dicarboxylic acid or derivatives
- Amino acid
- Alkylthiol
- Carboximidic acid
- Carboximidic acid derivative
- Carboxylic acid
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Organic nitrogen compound
- Organooxygen compound
- Organonitrogen compound
- Organosulfur compound
- Primary aliphatic amine
- Primary amine
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Carbonyl group
- Amine
- Organic oxygen compound
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Solid |
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Charge | 0 |
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Melting point | Not Available |
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Experimental Properties | Property | Value | Reference |
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Water Solubility | Not Available | PhysProp | LogP | Not Available | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations | |
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Organoleptic Properties | Not Available |
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SMPDB Pathways | |
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KEGG Pathways | |
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SMPDB Reactions | |
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KEGG Reactions | |
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Concentrations |
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Intracellular Concentrations | Not Available |
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Extracellular Concentrations | Not Available |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-054t-1920100000-5ce9a082971db6d9e2e9 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-054t-1920100000-5ce9a082971db6d9e2e9 | JSpectraViewer | MoNA | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-053u-9630000000-344be03dbe2132b00c88 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-00b9-8494000000-88b1eea1e1badaee084b | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0udi-0090000000-50bd1555ededc1afde80 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0udi-0290000000-385ca433f03af7530f47 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0ue9-5490000000-95d45a9cd2bb6249d3a2 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-001i-9510000000-5f29ca903abe05256c83 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-001i-9510000000-5f29ca903abe05256c83 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-0002-1490000000-bfce673369358b8079e9 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0690000000-c49357f0d28683125b6d | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 30V, Negative | splash10-002b-2490000000-41c54aabf6acd4d3b53e | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-014j-9050000000-1137fb3c62232376669c | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-05fr-1790000000-2aaa1344429a2297cc6b | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00di-4920000000-4ad42780853d5599c05b | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05fr-9400000000-b67fd0eaf646aa8f47b3 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000t-1390000000-e723899e4ca71bda7600 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00sj-3960000000-9a2f96ad7d24e7546315 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00e9-9300000000-e14b428bbb5b63d3ae06 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00b9-0910000000-302a05e4e453b27bad64 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004j-3900000000-da869ba294aa1d1e7c49 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-000x-9100000000-4bc7ff3637ea175068f0 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0zmi-0960000000-675f718188f5caad73ab | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-9600000000-13ddc5ab8de093dd11ab | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-001i-9100000000-8b8a5550fa1112649784 | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | JSpectraViewer |
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References |
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References: | - UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
- 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
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Synthesis Reference: | Bridge, Wallace John; Zarka, Martin Hani. Enzymic production of g-glutamylcysteine. PCT Int. Appl. (2006), 76pp. |
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External Links: | |
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