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Record Information
Version	2.0
Creation Date	2012-05-31 13:03:49 -0600
Update Date	2015-09-13 12:56:09 -0600
Secondary Accession Numbers	ECMDB01049
Identification
Name:	gamma-Glutamylcysteine
Description	G-Glutamylcysteine is a product of enzyme glutamate-cysteine ligase [EC 6.3.2.2] and a substrate of enzyme glutathione synthase [EC 6.3.2.3] in glutamate metabolism pathway (KEGG).
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xb056786c> Close
Synonyms:	γ-glutamylcysteine γ-L-glutamyl-L-cysteine (Des-Gly)-Glutathione 3GC 5-L-Glutamyl-L-cysteine 5-L-Glutamylcysteine g-Glu-cys G-Glutamylcysteine G-L-Glutamyl-L-cysteine Gamma-Glu-cys Gamma-Glutamylcysteine Gamma-L-Glutamyl-L-cysteine H-g-Glu-cys-OH H-gamma-Glu-Cys-OH H-Glu(Cys-OH)-OH H-γ-Glu-cys-OH L-g-Glutamyl-L-cysteine L-g-Glutamylcysteine L-gamma-Glutamyl-L-cysteine L-gamma-Glutamylcysteine L-γ-Glutamyl-L-cysteine L-γ-Glutamylcysteine N-(1-Carboxy-2-mercaptoethyl)-L-Glutamine N-L-g-Glutamyl-L-cysteine N-L-gamma-Glutamyl-L-Cysteine N-L-γ-Glutamyl-L-cysteine XN-L-g-glutamyl-Glutamine XN-L-gamma-glutamyl-Glutamine XN-L-γ-Glutamyl-glutamine γ-Glu-cys γ-Glutamylcysteine γ-L-Glutamyl-L-cysteine
Chemical Formula:	C8H14N2O5S
Weight:	Average: 250.272 Monoisotopic: 250.062342258
InChI Key:	RITKHVBHSGLULN-WHFBIAKZSA-N
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
CAS number:	636-58-8
IUPAC Name:	(2S)-2-amino-4-{[(1R)-1-carboxy-2-sulfanylethyl]carbamoyl}butanoic acid
Traditional IUPAC Name:	gamma-glutamylcysteine
SMILES:	N[C@@H](CCC(=O)N[C@@H](CS)C(O)=O)C(O)=O
Chemical Taxonomy
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.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Carboxylic acids and derivatives
Sub Class	Amino acids, peptides, and analogues
Direct Parent	N-acyl-alpha amino acids
Alternative Parents	Cysteine and derivatives L-alpha-amino acids Fatty acids and conjugates Dicarboxylic acids and derivatives Amino acids Propargyl-type 1,3-dipolar organic compounds Carboxylic acids Carboximidic acids Alkylthiols Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
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
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	gamma-glutamylcysteine (CHEBI:17515 )
Physical Properties
State:	Solid
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 2.62 g/L ALOGPS logP -2.5 ALOGPS logP -3.8 ChemAxon logS -2 ALOGPS pKa (Strongest Acidic) 1.91 ChemAxon pKa (Strongest Basic) 9.24 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 6 ChemAxon Hydrogen Donor Count 5 ChemAxon Polar Surface Area 129.72 Ų ChemAxon Rotatable Bond Count 7 ChemAxon Refractivity 56.31 m³·mol⁻¹ ChemAxon Polarizability 23.36 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	Adenosine triphosphate + L-Cysteine + L-Glutamate <> ADP + gamma-Glutamylcysteine + Hydrogen ion + Phosphate Adenosine triphosphate + gamma-Glutamylcysteine + Glycine <> ADP + Glutathione + Hydrogen ion + Phosphate Adenosine triphosphate + gamma-Glutamylcysteine + Glycine <> ADP + Phosphate + Glutathione Adenosine triphosphate + L-Glutamate + L-Cysteine <> ADP + Phosphate + gamma-Glutamylcysteine Glycine + gamma-Glutamylcysteine + Adenosine triphosphate > Hydrogen ion + Glutathione + Phosphate + ADP L-Cysteine + L-Glutamate + Adenosine triphosphate > Hydrogen ion + gamma-Glutamylcysteine + Phosphate + ADP Adenosine triphosphate + L-Glutamate + L-Cysteine > ADP + Inorganic phosphate + gamma-Glutamylcysteine Adenosine triphosphate + gamma-Glutamylcysteine + Glycine > ADP + Inorganic phosphate + Glutathione L-Glutamic acid + Adenosine triphosphate + L-Cysteine + L-Glutamate > Adenosine diphosphate + Phosphate + Hydrogen ion + gamma-Glutamylcysteine + ADP gamma-Glutamylcysteine + Glycine + Adenosine triphosphate > Hydrogen ion + Phosphate + Adenosine diphosphate + Glutathione + ADP Adenosine triphosphate + gamma-Glutamylcysteine + Glycine <> ADP + Glutathione + Hydrogen ion + Phosphate Adenosine triphosphate + L-Cysteine + L-Glutamate <> ADP + gamma-Glutamylcysteine + Hydrogen ion + Phosphate Adenosine triphosphate + L-Cysteine + L-Glutamate <> ADP + gamma-Glutamylcysteine + Hydrogen ion + Phosphate
SMPDB Pathways:	Glutathione metabolism PW000833 glutathione metabolism II PW001927 glutathione metabolism III PW002018
KEGG Pathways:	Glutathione metabolism ec00480 Metabolic pathways eco01100
EcoCyc Pathways:	glutathione biosynthesis GLUTATHIONESYN-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) splash10-054t-1920100000-5ce9a082971db6d9e2e9 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-054t-1920100000-5ce9a082971db6d9e2e9 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-053u-9630000000-344be03dbe2132b00c88 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive splash10-00b9-8494000000-88b1eea1e1badaee084b View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) splash10-0udi-0090000000-50bd1555ededc1afde80 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) splash10-0udi-0290000000-385ca433f03af7530f47 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) splash10-0ue9-5490000000-95d45a9cd2bb6249d3a2 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive splash10-001i-9510000000-5f29ca903abe05256c83 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF , positive splash10-001i-9510000000-5f29ca903abe05256c83 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 20V, Negative splash10-0002-1490000000-bfce673369358b8079e9 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 10V, Negative splash10-0002-0690000000-c49357f0d28683125b6d View in MoNA LC-MS/MS LC-MS/MS Spectrum - 30V, Negative splash10-002b-2490000000-41c54aabf6acd4d3b53e View in MoNA LC-MS/MS LC-MS/MS Spectrum - 40V, Negative splash10-014j-9050000000-1137fb3c62232376669c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-05fr-1790000000-2aaa1344429a2297cc6b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-00di-4920000000-4ad42780853d5599c05b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-05fr-9400000000-b67fd0eaf646aa8f47b3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-000t-1390000000-e723899e4ca71bda7600 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-00sj-3960000000-9a2f96ad7d24e7546315 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-00e9-9300000000-e14b428bbb5b63d3ae06 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-00b9-0910000000-302a05e4e453b27bad64 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004j-3900000000-da869ba294aa1d1e7c49 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-000x-9100000000-4bc7ff3637ea175068f0 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0zmi-0960000000-675f718188f5caad73ab View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-001i-9600000000-13ddc5ab8de093dd11ab View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-001i-9100000000-8b8a5550fa1112649784 View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,13C] 2D NMR Spectrum Not Available View in JSpectraViewer
References
References:	Andersson A, Isaksson A, Brattstrom L, Hultberg B: Homocysteine and other thiols determined in plasma by HPLC and thiol-specific postcolumn derivatization. Clin Chem. 1993 Aug;39(8):1590-7. Pubmed: 8353942 Andersson A, Isaksson A, Hultberg B: Homocysteine export from erythrocytes and its implication for plasma sampling. Clin Chem. 1992 Jul;38(7):1311-5. Pubmed: 1623596 Atamna H, Ginsburg H: The malaria parasite supplies glutathione to its host cell--investigation of glutathione transport and metabolism in human erythrocytes infected with Plasmodium falciparum. Eur J Biochem. 1997 Dec 15;250(3):670-9. Pubmed: 9461289 Diaz-Hernandez JI, Almeida A, Delgado-Esteban M, Fernandez E, Bolanos JP: Knockdown of glutamate-cysteine ligase by small hairpin RNA reveals that both catalytic and modulatory subunits are essential for the survival of primary neurons. J Biol Chem. 2005 Nov 25;280(47):38992-9001. Epub 2005 Sep 23. Pubmed: 16183645 Efferth T, Volm M: Glutathione-related enzymes contribute to resistance of tumor cells and low toxicity in normal organs to artesunate. In Vivo. 2005 Jan-Feb;19(1):225-32. Pubmed: 15796179 Iida M, Yasuhara T, Mochizuki H, Takakura H, Yanagisawa T, Kubo H: Two Japanese brothers with hereditary gamma-glutamyl transpeptidase deficiency. J Inherit Metab Dis. 2005;28(1):49-55. Pubmed: 15702405 Kaarteenaho-Wiik R, Kinnula VL: Distribution of antioxidant enzymes in developing human lung, respiratory distress syndrome, and bronchopulmonary dysplasia. J Histochem Cytochem. 2004 Sep;52(9):1231-40. Pubmed: 15314090 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882 Levonen AL, Lapatto R, Saksela M, Raivio KO: Expression of gamma-glutamylcysteine synthetase during development. Pediatr Res. 2000 Feb;47(2):266-70. Pubmed: 10674357 Lochman P, Adam T, Friedecky D, Hlidkova E, Skopkova Z: High-throughput capillary electrophoretic method for determination of total aminothiols in plasma and urine. Electrophoresis. 2003 Apr;24(7-8):1200-7. Pubmed: 12707912 Lou MF, Dickerson JE Jr, Tung WH, Wolfe JK, Chylack LT Jr: Correlation of nuclear color and opalescence with protein S-thiolation in human lenses. Exp Eye Res. 1999 May;68(5):547-52. Pubmed: 10328968 Martensson J, Kagedal B, Larsson A: Sulphur amino-acid degradation in subjects with hereditary glutathione synthetase deficiency (5-oxoprolinuria). Eur J Clin Invest. 1985 Dec;15(6):371-4. Pubmed: 3938407 Martensson J: Method for determination of free and total glutathione and gamma-glutamylcysteine concentrations in human leukocytes and plasma. J Chromatogr. 1987 Sep 4;420(1):152-7. Pubmed: 3667817 Njalsson R, Ristoff E, Carlsson K, Winkler A, Larsson A, Norgren S: Genotype, enzyme activity, glutathione level, and clinical phenotype in patients with glutathione synthetase deficiency. Hum Genet. 2005 Apr;116(5):384-9. Epub 2005 Feb 17. Pubmed: 15717202 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 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 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 Zinellu A, Sotgia S, Posadino AM, Pasciu V, Perino MG, Tadolini B, Deiana L, Carru C: Highly sensitive simultaneous detection of cultured cellular thiols by laser induced fluorescence-capillary electrophoresis. Electrophoresis. 2005 Mar;26(6):1063-70. Pubmed: 15706569
Synthesis Reference:	Bridge, Wallace John; Zarka, Martin Hani. Enzymic production of g-glutamylcysteine. PCT Int. Appl. (2006), 76pp.
Material Safety Data Sheet (MSDS)	Download (PDF)
Links
External Links:	Resource Link CHEBI ID 17515 HMDB ID HMDB01049 Pubchem Compound ID 123938 Kegg ID C00669 ChemSpider ID 110467 Wikipedia ID Gamma-Glutamylcysteine BioCyc ID L-GAMMA-GLUTAMYLCYSTEINE EcoCyc ID L-GAMMA-GLUTAMYLCYSTEINE Ligand Expo 3GC

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