gamma-Glutamylcysteinylglycine

Base Information

• Chemical Name: gamma-Glutamylcysteinylglycine
• CAS No.: 70-18-8
• Molecular Formula: C10H17N3O6S
• Molecular Weight: 307.327
• Hs Code.: 29309070
• NSC Number: 647529,400639
• DSSTox Substance ID: DTXSID70859082
• Nikkaji Number: J1.025.254G
• Wikidata: Q105246729
• ChEMBL ID: CHEMBL100476
• Mol file: 70-18-8.mol

Synonyms:76946-74-2;gamma-Glutamylcysteinylglycine;2-amino-4-({1-[(carboxymethyl)carbamoyl]-2-sulfanylethyl}carbamoyl)butanoic acid;NSC647529;GLUTATHIONE REDUCED, IMMOBILIZED ON AGAROSE CL-4B;GLUTATHIONE-(GLYCINE-13C2,15N1);Glycine, N-(N-DL-gamma-glutamyl-DL-cysteinyl)-;glutathionate ion;glutathionate anion;2-amino-5-[[2-(carboxymethylamino)-2-oxo-1-(sulfanylmethyl)ethyl]amino]-5-oxo-pentanoic acid;L-Glutathione (Reduced);MFCD00065939;NSC400639;Glutathionic acid;re-duced glutathione;Glutathionic acid ion;Glutathionic acid anion;Glutathionic acid(1-);Glycine, N-(N-L-.gamma.-glutamyl-L-cysteinyl)-;SCHEMBL9168;MLS000028525;CHEMBL100476;DTXSID70859082;CHEBI:177535;AMY30103;BCP13980;BBL023772;STL356049;.gamma.-L-Glutamyl-L-cysteinylglycine;AKOS015962125;L-gamma-glutamyl-L-cysteinyl-glycine;NSC-400639;NSC-647529;PB43312;AC-15843;AC-37034;AS-19360;SMR000058262;SY012937;FT-0627837;FT-0669013;EN300-71939;F8889-1694;gamma-L-Glu-L-Cys-Gly;GSH;L-Glutathione;Glutathion;4,7-Dioxo-5-(mercaptomethyl)-10-amino-3,6-diazaundecanedioic acid;Glutaramic acid, 2-amino-N-[1-[(carboxymethyl)carbamoyl]-2-mercapto-;N~5~-(2-((Carboxymethyl)amino)-1-(mercaptomethyl)-2-oxoethyl)glutamine;2-amino-4-({1-[(carboxymethyl)carbamoyl]-2-sulfanylethyl}carbamoyl)butanoicacid;2-amino-5-(1-(carboxymethylamino)-3-mercapto-1-oxopropan-2-ylamino)-5-oxopentanoic acid;2-amino-5-[[1-(carboxymethylamino)-1-oxo-3-sulanylpropan-2-yl]amino]-5-oxopentanoic acid;(2R)-2-amino-5-[[(2S)-1-(carboxymethylamino)-1-oxo-3-sulfanylpropan-2-yl]amino]-5-oxopentanoic acid

Chemical Property of gamma-Glutamylcysteinylglycine

Chemical Property:

• Appearance/Colour: White cryst. powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 192-195 °C (dec.)(lit.)
• Refractive Index: -17 ° (C=2, H2O)
• Boiling Point: 754.492 °C at 760 mmHg
• PKA: pK1 2.12; pK2 3.53; pK3 8.66; pK4 9.12(at 25℃)
• Flash Point: 410.102 °C
• PSA: 197.62000
• Density: 1.441 g/cm³
• LogP: -0.72400
• Storage Temp.: 2-8°C
• Solubility.: H2O: 50 mg/mL
• Water Solubility.: soluble
• XLogP3: -4.5
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 307.08380644
• Heavy Atom Count: 20
• Complexity: 389

Purity/Quality:

99% up, ^*data from raw suppliers

Reduced Glutathione ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 68-36/37/38
• Safety Statements: 24/25-36/37/39-27-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(CC(=O)NC(CS)C(=O)NCC(=O)O)C(C(=O)O)N
• Description: Glutathione (GSH) is the most abundant non-protein thiol. Glutathione is abundant in the liver and kidney and is present at lower levels in the brain.
• Role: It plays a crucial role in the antioxidant defense system and the maintenance of redox homeostasis in neurons. Glutathione is a major antioxidant maintaining redox homeostasis in cells.
• Association with Neurodegenerative Diseases: GSH depletion in the brain is common in neurodegenerative diseases like Alzheimer鈥檚 and Parkinson鈥檚, leading to neurodegeneration.
• Regulation: Excitatory amino acid carrier 1 (EAAC1) regulates neuronal GSH production.
• Historical Background: Discovery: Glutathione was discovered in 1921 by Frederick G. Hopkins.; Structure: It was determined to be a tripeptide containing Glutamate (Glu), Cysteine (Cys), and Glycine (Gly) by Edward C. Kendall in 1929.; Synthesis: Vincent du Vigneaud synthesized GSH in 1936.
• Functions: Antioxidant System Maintenance; Redox Balance; Cysteine Transport/Storage; Cell Signaling; Regulation of Enzyme Activities; Gene Expression; Cell Differentiation/Proliferation
• Mechanisms in the Brain: The regulatory system for GSH synthesis in the brain differs from that in peripheral tissues.

Technology Process of gamma-Glutamylcysteinylglycine

There total 158 articles about gamma-Glutamylcysteinylglycine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 40.0%

methylmercury-L-glutathionate + 1-(2-hydroxyethyl)-3-methyl-1H-benzo[d]imidazole-2(3H)-thione → GLUTATHIONE (70-18-8) + mercury sulfide + dimethylmercury (593-74-8) + 1-(2-hydroxyethyl)-3-methyl-1H-benzo[d]imidazol-2(3H)-one (2033-53-6)

Guidance literature:

methylmercury-L-glutathionate; 1-(2-hydroxyethyl)-3-methyl-1H-benzo[d]imidazole-2(3H)-thione; In water; acetonitrile; at 37 ℃; for 1h;

With sodium hydrogencarbonate; In water; acetonitrile; at 37 ℃; for 5h;

DOI:10.1002/chem.201605238

Reference yield:

(S)-2-Amino-4-[(R)-1-(carboxymethyl-carbamoyl)-2-(hydroxy-phenyl-methylsulfanyl)-ethylcarbamoyl]-butyric acid → GLUTATHIONE (70-18-8) + benzaldehyde (100-52-7)

Guidance literature:

In water; at 25 ℃; Equilibrium constant;

DOI:10.1021/ja00505a030

Reference yield:

L-γ-glutamyl->S-((1Ξ,2Ξ)-1,2-dihydroxy-3-phosphonooxy-propyl)-L-cysteinyl->glycine → DL-glyceraldehyde 3-phosphate (142-10-9,591-57-1,20283-52-7,591-59-3) + GLUTATHIONE (70-18-8)

Guidance literature:

In water; at 25 ℃; Equilibrium constant;

DOI:10.1021/ja00505a030

upstream raw materials:

oxidized glutathione

1,3-dimercapto-2-propanol

diothiothreitol

2-hydroxyethanethiol

Downstream raw materials:

N⁵-((R)-3-(acetylthio)-1-((carboxymethyl)amino)-1-oxopropan-2-yl)-L-glutamine

oxidized glutathione

Oxidized glutathione

L-glutamic acid

Refernces

• 1、 Mezyk, Stephen P.. "Rate constant determination for the reaction of hydroxyl and glutathione thiyl radicals with glutathione in aqueous solution". . p. 8861 - 8866. Retrieved 1996.
• 2、 Bienvenu, Céline,Greiner, Jacques,Vierling, Pierre,Giorgio, Christophe Di. "Convenient supported recyclable material based on dihydrolipoyl-residue for the reduction of disulfide derivatives". . p. 3309 - 3311. Retrieved 2010.
• 3、 Samarasinghe, Kusal T. G.,Munkanatta Godage, Dhanushka N. P.,Vanhecke, Garrett C.,Ahn, Young-Hoon. "Metabolic synthesis of clickable glutathione for chemoselective detection of glutathionylation". . p. 11566 - 11569. Retrieved 2014.
• 4、 Dereven'kov, Ilia A.,Hannibal, Luciana,Molodtsov, Pavel A.,Branzanic, Adrian M.V.,Silaghi-Dumitrescu, Radu,Makarov, Sergei V.. "Kinetic, spectroscopic and in silico characterization of the first step of the reaction between glutathione and selenite". . . Retrieved 2020.
• 5、 Marsch, Glenn A.,Mundkowski, Ralf G.,Morris, Brent J.,Manier, M. Lisa,Hartman, Melanie K.,Guengerich, F. Peter. "Characterization of nucleoside and DNA adducts formed by S-(1-Acetoxymethyl)glutathione and implications for dihalomethane - Glutathione conjugates". . p. 600 - 608. Retrieved 2001.
• 6、 De Keczer, Steve A.,Voronin, Tatyana,Yao, Jennifer,Zhang, Fang-Jie,Masjedizadeh, Mohammad R.. "Simple single-step single-enzyme synthesis of [14C]-GSH". . p. 110 - 112. Retrieved 2010.
• 7、 Kato, Masahiro,Yamamoto, Hitoshi,Okamura, Taka-Aki,Maoka, Nobuko,Masui, Ryoji,Kuramitsu, Seiki,Ueyama, Norikazu. "Inhibition of thermus thermophilus HB8 thioredoxin activity by platinum(II)". . p. 1023 - 1026. Retrieved 2005.
• 8、 Meder, Fabian,Hintz, Henrik,Koehler, Yvonne,Schmidt, Maike M.,Treccani, Laura,Dringen, Ralf,Rezwan, Kurosch. "Adsorption and orientation of the physiological extracellular peptide glutathione disulfide on surface functionalized colloidal alumina particles". . p. 6307 - 6316. Retrieved 2013.
• 9、 Chen, Zhenzhen,Jiang, Zhongyao,Chen, Nan,Shi, Qian,Tong, Lili,Kong, Fanpeng,Cheng, Xiufen,Chen, Hao,Wang, Chu,Tang, Bo. "Target discovery of ebselen with a biotinylated probe". . p. 9506 - 9509. Retrieved 2018.
• 10、 Nakashima,Nishida,Nakatsuji,Akiyama. "Development and application of organic reagents for analysis. VIII. Determination of biological thiols with a new fluorogenic thiol-selective reagent, N-(p-[2-(6-dimethylamino)benzofuranyl]phenyl)maleimide.". . p. 1678 - 1683. Retrieved 1986.