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Chemical Structure| 636-58-8 Chemical Structure| 636-58-8
Chemical Structure| 636-58-8

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Gamma-glutamylcysteine is a dipeptide containing cysteine and glutamic acid, serving as a precursor to glutathione (GSH). It acts as a cofactor for glutathione peroxidase (GPx) to increase GSH levels.

Synonyms: γ-Glu-Cys

4.5 *For Research Use Only !

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Product Details of Gamma-glutamylcysteine

CAS No. :636-58-8
Formula : C8H14N2O5S
M.W : 250.27
SMILES Code : O=C(O)[C@@H](N)CCC(N[C@H](C(O)=O)CS)=O
Synonyms :
γ-Glu-Cys
MDL No. :MFCD00237863

Safety of Gamma-glutamylcysteine

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H319-H332-H372-H400
Precautionary Statements:P260-P264-P270-P273-P280-P301+P312+P330-P304+P312-P305+P351+P338-P314-P337+P313-P391-P501
Class:9
UN#:3077
Packing Group:

Application In Synthesis of Gamma-glutamylcysteine

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 636-58-8 ]

[ 636-58-8 ] Synthesis Path-Downstream   1~47

  • 2
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  • [ 4510-09-2 ]
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  • [ 100051-89-6 ]
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  • 7
  • [ 95014-75-8 ]
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  • 8
  • [ 636-58-8 ]
  • [ 108-24-7 ]
  • N,S-bis-acetyl-γ-L-glutamyl-L-cysteine [ No CAS ]
  • 9
  • [ 190063-00-4 ]
  • [ 636-58-8 ]
  • 10
  • [ 636-58-8 ]
  • [ 507-09-5 ]
  • N,S-bis-acetyl-γ-L-glutamyl-L-cysteine [ No CAS ]
  • (S)-4-((R)-2-Acetylsulfanyl-1-carboxy-ethylcarbamoyl)-2-amino-butyric acid [ No CAS ]
  • 11
  • [ 70-18-8 ]
  • [ 636-58-8 ]
  • [ 86220-45-3 ]
  • [ 95014-75-8 ]
  • [ 100922-53-0 ]
  • [ 118433-03-7 ]
  • 14
  • [ 52-90-4 ]
  • L-glutamate [ No CAS ]
  • [ 636-58-8 ]
  • 15
  • N-<L-4-benzyloxycarbonylamino-4-methoxycarbonyl-butyryl->-L-cysteine ethyl ester [ No CAS ]
  • [ 636-58-8 ]
  • 16
  • [ 56-41-7 ]
  • [ 70-18-8 ]
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  • [ 34286-34-5 ]
  • 17
  • [ 56-45-1 ]
  • [ 70-18-8 ]
  • [ 636-58-8 ]
  • γ-L-glutamyl-L-cysteinyl-L-serine [ No CAS ]
  • 18
  • [ 636-58-8 ]
  • [ 50700-49-7 ]
  • 3-(γ-L-glutamyl-L-cystein-S-yl)acetaminophen [ No CAS ]
  • 19
  • [ 636-58-8 ]
  • [ 556-50-3 ]
  • [ 52-90-4 ]
  • 20
  • (R)-3-[(S)-4-Carboxy-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-butyryl]-2-methyl-thiazolidine-4-carboxylic acid [ No CAS ]
  • [ 636-58-8 ]
  • 22
  • [ 27025-41-8 ]
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  • 23
  • [ 52-90-4 ]
  • [ 142-47-2 ]
  • [ 636-58-8 ]
  • 24
  • [ 636-58-8 ]
  • [ 70-18-8 ]
  • N,N'-bis-γ-glutamylcystinylglycine [ No CAS ]
  • 25
  • [ 52-90-4 ]
  • glutamate [ No CAS ]
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  • 26
  • [ 636-58-8 ]
  • [ 56-39-3 ]
  • [ 1234937-76-8 ]
  • 27
  • [ 636-58-8 ]
  • [ 56-39-3 ]
  • [ 1234937-73-5 ]
  • [ 1234937-76-8 ]
  • 28
  • [ 636-58-8 ]
  • [ 56-39-3 ]
  • [ 1234937-73-5 ]
  • 29
  • [ 636-58-8 ]
  • [ 7149-49-7 ]
  • [ 169136-26-9 ]
  • 30
  • [ 636-58-8 ]
  • [ 643-79-8 ]
  • [ 1282511-37-8 ]
  • 31
  • [ 636-58-8 ]
  • [ 71-00-1 ]
  • C14H21N5O8S [ No CAS ]
  • 32
  • [ 636-58-8 ]
  • [ 534-30-5 ]
  • C17H27N5O8S [ No CAS ]
  • 33
  • [ 636-58-8 ]
  • C33H31N7O12S [ No CAS ]
  • 34
  • [ 636-58-8 ]
  • C32H30N4O12S [ No CAS ]
  • 35
  • [ 63-68-3 ]
  • [ 636-58-8 ]
  • C13H23N3O6S2 [ No CAS ]
  • 36
  • [ 63-68-3 ]
  • [ 636-58-8 ]
  • C35H36N4O12S2 [ No CAS ]
  • 37
  • [ 72-18-4 ]
  • [ 636-58-8 ]
  • C13H23N3O6S [ No CAS ]
  • 38
  • [ 636-58-8 ]
  • [ 98891-36-2 ]
  • C14H21N3O6S [ No CAS ]
  • 39
  • [ 636-58-8 ]
  • [ 23235-01-0 ]
  • C13H19N3O6S [ No CAS ]
  • 40
  • [ 636-58-8 ]
  • [ 23235-01-0 ]
  • C35H32N4O12S [ No CAS ]
  • 41
  • [ 56-41-7 ]
  • [ 636-58-8 ]
  • [ 34286-34-5 ]
  • 42
  • [ 636-58-8 ]
  • [ 105661-40-3 ]
  • C11H18N6O6S [ No CAS ]
  • 43
  • [ 4144-22-3 ]
  • [ 636-58-8 ]
  • [ 76-05-1 ]
  • C16H25N3O7S*C2HF3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% Glu-Cys (15.3 mg, 0.06 mmol, 1.0 eq.) and NaOH (2.4 mg, 0.06 mmol, 1.0 eq.) were stirredin water (0.4 mL), to this N-tert-butyl-maleimide (9.4 mg, 8.8 1iL, 0.06 mmol, 1.0 eq.) wasadded and the resulting solution stirred at RT for 4.5 h. After this time, the reaction solutionwas lyophilized and the resulting solid was purified by semi-preparative HPLC (AgilentZORBAX 3005B-C18 column; 95:5:0.1 - 5:95:0.1; H20 : MeCN: TFA) to afford 1(mixture of diastereoisomers) as a colourless solid (19.8 mg, 63%): Ri? 0.8 (50:50 acetonitrilewater (RP)); [a] -6.4 (c 1.1, H20); vmax/cm? (neat) 1739.3 (s), 1367.7 (w), 1215.6 (w); ?HNIVIR (500 MHz; D20): s/ppm 4.71-4.63 (m, 1H, Cys-ct-CI]), 4.04 (dd, 1H, J7.0 Hz, J6.5Hz, Glu-ct-CI]), 3.92-3.85 (m, 1H, Succinimide-CI]), 3.37 (dd, 0.5H, J 14.1 Hz, J4.6 Hz,Cys-f3-CH2), 3.27 (dd, 0.5H, J 14.1 Hz, J4.6 Hz, Cys-f3-CH2), 3.23-3.10 (m, 1.5H, Cys-13-CH2, Succinimide-CH2), 3.04 (dd, 0.5H, J 14.1 Hz, J8.7 Hz, Cys-f3-CH2), 2.64-2.52 (m, 3H,Glu-Y-CH2, Succinimide-CH2), 2.3 1-2.15 (m, 2H, Glu-f3-CH2), 1.54 (s, 4.5H, NC(CH3)3),1.53 (s, 4.5H, NC(CH3)3); ?9F NMR (decoupled) (376.6 MFIz; D20): s/ppm -75.7(OCOCF3); ?3C NMR (128.5 MFIz; D20): s/ppm 180.1 (Succinimide-CO), 180.0(Succinimide-CO), 179.1 (Succinimide-CO), 179.0 (Succinimide-CO), 174.3 (Glu-CO),174.3 (Glu-CO), 173.5 (Cys-COOH),173.5 (Cys-COOH), 172.0 (Glu-COOH), 163.0 (q, J35.3 Hz, OCOCF3), 116.3 (q, J291.5 Hz, OCOCF3), 59.2 (NC(CH3)3), 59.2 (NC(CH3)3),52.6 (Glu-ct-CH), 52.2 (Cys-ct-CH), 40.9 (Succinimide-CH), 39.9 (Succinimide-CH), 36.3(Succinimide-CH2), 35.8 (Succinimide-CH2), 32.3 (Cys-f3-CH2), 31.8 (Cys-f3-CH2), 31.0(Glu-Y-CH2), 27.3 (NC(CH3)3), 25.7 (Glu-f3-CH2); HRIVIS m/z (ESIj (Found: [M+H]404.14836. C,6H2607N35 requires M404.14860); m/z (ESj 404 ([M+H], 100%);Analytical HPLC 220 nm (Acclaim 120 C18 RP LC Column; 95:5:0.1 - 5:95:0.1; H20MeCN: TFA) Ret. Time = 9.094 mi Purity: 98.57%.
  • 44
  • [ 16338-48-0 ]
  • [ 636-58-8 ]
  • C13H21N3O6S [ No CAS ]
  • 45
  • [ 636-58-8 ]
  • [ 107903-44-6 ]
  • C14H23N3O7S [ No CAS ]
  • 46
  • [ 636-58-8 ]
  • C8H11NO4 [ No CAS ]
  • C16H23N3O8S [ No CAS ]
  • 47
  • [ 636-58-8 ]
  • [ 30954-70-2 ]
  • C36H22O8 [ No CAS ]
  • C26H24N2O9S [ No CAS ]
 

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