GAMMA-GLU-CYS TRIFLUOROACETATE SALT

Base Information

• Chemical Name: GAMMA-GLU-CYS TRIFLUOROACETATE SALT
• CAS No.: 636-58-8
• Deprecated CAS: 6710-20-9,190063-04-8,910891-06-4,1296212-88-8
• Molecular Formula: C8H14N2O5S
• Molecular Weight: 250.276
• European Community (EC) Number: 636-320-8
• UNII: M984VJS48P
• DSSTox Substance ID: DTXSID90212978
• Nikkaji Number: J40.069F
• Wikipedia: Gamma-L-Glutamyl-L-cysteine
• Wikidata: Q288236
• Metabolomics Workbench ID: 37569
• ChEMBL ID: CHEMBL460831
• Mol file: 636-58-8.mol

Synonyms:gamma-glutamylcysteine;H-GLU(CYS-OH)-OH TFA;GAMMA-GLU-CYS TRIFLUOROACETATE SALT;(DES-GLY)-GLUTATHIONE TFA (REDUCED);G-glu-cys trifluoroacetate;des-gly-glutathione reduced form;γ-glu-cys;2-amino-5-(1-carboxy-2-sulfanyl-ethyl)amino-5-oxo-pentanoic acid

Chemical Property of GAMMA-GLU-CYS TRIFLUOROACETATE SALT

Chemical Property:

• Vapor Pressure: 1.45E-15mmHg at 25°C
• Melting Point: 167℃
• Refractive Index: 1.57
• Boiling Point: 592.4oC at 760 mmHg
• PKA: 2.21±0.10(Predicted)
• Flash Point: 312.1oC
• PSA: 168.52000
• Density: 1.436g/cm3
• LogP: -0.23110
• Storage Temp.: −20°C
• XLogP3: -3.8
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 250.06234272
• Heavy Atom Count: 16
• Complexity: 284

Purity/Quality:

98%,99%, ^*data from raw suppliers

Gamma-L-glutamyl-L-cysteine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(CC(=O)NC(CS)C(=O)O)C(C(=O)O)N
• Isomeric SMILES: C(CC(=O)N[C@@H](CS)C(=O)O)[C@@H](C(=O)O)N
• Description: Gamma-glutamylcysteine (γ-Glutamylcysteine) is a cysteine and glutamic acid-containing dipeptide that is a precursor to glutathione (GSH). Gamma-glutamylcysteine is a cofactor for glutathione peroxidase (GPx) to increase GSH levels.
• Uses: γ-Glu-Cys is used to study the active sites and kinetics of glutathione synthetase(s). It has also been used for the extraction and quantification of low molecular weight thiols from Arabidopsis tissues.

Technology Process of GAMMA-GLU-CYS TRIFLUOROACETATE SALT

There total 19 articles about GAMMA-GLU-CYS TRIFLUOROACETATE SALT 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: 55.5%

L-Cysteine (52-90-4) + monosodium L-glutamate (142-47-2) → N-L-γ-glutamyl-L-cysteine (636-58-8,6710-20-9)

Guidance literature:

With adenosine 5'-triphosphate sodium salt; magnesium chloride; bovine serum albumin; at 30 ℃; for 24h; γ-glutamylcysteine synthetase from Proteus mirabilis, pH 8.5;

Reference yield:

GLUTATHIONE (70-18-8) → N-L-γ-glutamyl-L-cysteine (636-58-8,6710-20-9) + H-γ-L-Glu-L-Cys-γ-L-Glu-L-Cys-γ-L-Glu-L-Cys-Gly-OH (cadystin A <1>) (86220-45-3) + H-γ-L-Glu-L-Cys-γ-L-Glu-L-Cys-Gly-OH (cadystin B <2>) (95014-75-8) + (γ-Glu-Cys)2 (100922-53-0) + (γ-Glu-Cys)3 (118433-03-7)

Guidance literature:

In water; at 37 ℃; for 4h; transformation by carboxypeptidase Y; pH 9.7;

DOI:10.1271/bbb.60.1193

Reference yield:

N-phthaloyl-L-glutamic anhydride (25830-77-7,3085-92-5) → N-L-γ-glutamyl-L-cysteine (636-58-8,6710-20-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) BSTFA / 1.) CH₃CN, 50 min, 2.) CH₃CN

2: 2.0 M NH₂NH₂*H₂O, Et₃N / methanol; H₂O

3: 1.) Hg(OAc)2, 2.) H₂S (gas) / 1.) H₂O, 38-41 deg C, 2.5 h, 2.) H₂O, RT, 45 min

With hydrogen sulfide; mercury(II) diacetate; N,O-Bis(trimethylsilyl)trifluoroacetamide; hydrazine hydrate; triethylamine; In methanol; water;

DOI:10.1021/jm950674y

upstream raw materials:

(γEC)2

N-benzyloxycarbonyl-L-glutamic acid-5-hydrazide

S-benzyl-L-cysteine ethyl ester

(R)-3-L-γ-glutamyl-2,2-dimethyl-thiazolidine-4-carboxylic acid

Downstream raw materials:

(γEC)2

L-Cysteine

GLUTATHIONE

Refernces

• 1、 Nagasawa, Herbert T.,Cohen, Jonathan F.,Holleschau, Ann M.,Rathbun, William B.. "Augmentation of human and rat lenticular glutathione in vitro by prodrugs of γ-L-glutamyl-L-cysteine". . p. 1676 - 1681. Retrieved 1996.
• 2、 Miyake, Koichiro,Kakita, Shingo. "A novel catalytic ability of γ-glutamylcysteine synthetase of Escherichia coli and its application in theanine production". experimental part. p. 2677 - 2683. Retrieved 2010/09/11.