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L-Glutathione Reduced

Endogenous antioxidant CAS# 70-18-8

L-Glutathione Reduced

Catalog No. BCC8030----Order now to get a substantial discount!

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Chemical structure

L-Glutathione Reduced

3D structure

Chemical Properties of L-Glutathione Reduced

Cas No. 70-18-8 SDF Download SDF
PubChem ID 124886 Appearance Powder
Formula C10H17N3O6S M.Wt 307.32
Type of Compound Alkaloids Storage Desiccate at -20°C
Synonyms GSH
Solubility H2O : ≥ 60 mg/mL (195.24 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name (2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-1-oxo-3-sulfanylpropan-2-yl]amino]-5-oxopentanoic acid
SMILES C(CC(=O)NC(CS)C(=O)NCC(=O)O)C(C(=O)O)N
Standard InChIKey RWSXRVCMGQZWBV-WDSKDSINSA-N
Standard InChI InChI=1S/C10H17N3O6S/c11-5(10(18)19)1-2-7(14)13-6(4-20)9(17)12-3-8(15)16/h5-6,20H,1-4,11H2,(H,12,17)(H,13,14)(H,15,16)(H,18,19)/t5-,6-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of L-Glutathione Reduced

Them grape juice and wine.

Biological Activity of L-Glutathione Reduced

DescriptionGlutathione plays important roles in antioxidant defense, nutrient metabolism, and regulation of cellular events (including gene expression, DNA and protein synthesis, cell proliferation and apoptosis, signal transduction, cytokine production and immune response, and protein glutathionylation); glutathione deficiency contributes to oxidative stress, which plays a key role in aging and the pathogenesis of many diseases (including kwashiorkor, seizure, Alzheimer's disease, Parkinson's disease, liver disease, cystic fibrosis, sickle cell anemia, HIV, AIDS, cancer, heart attack, stroke, and diabetes).
TargetsDNA/RNA Synthesis | HIV | Immunology & Inflammation related

Protocol of L-Glutathione Reduced

Kinase Assay

Glutathione metabolism and its implications for health[Pubmed: 14988435]

J Nutr. 2004 Mar;134(3):489-92.

Glutathione (gamma-glutamyl-cysteinyl-glycine; GSH) is the most abundant low-molecular-weight thiol, and GSH/Glutathione disulfide is the major redox couple in animal cells. The synthesis of GSH from glutamate, cysteine, and glycine is catalyzed sequentially by two cytosolic enzymes, gamma-glutamylcysteine synthetase and GSH synthetase.
METHODS AND RESULTS:
Compelling evidence shows that GSH synthesis is regulated primarily by gamma-glutamylcysteine synthetase activity, cysteine availability, and GSH feedback inhibition. Animal and human studies demonstrate that adequate protein nutrition is crucial for the maintenance of GSH homeostasis. In addition, enteral or parenteral cystine, methionine, N-acetyl-cysteine, and L-2-oxothiazolidine-4-carboxylate are effective precursors of cysteine for tissue GSH synthesis. Glutathione plays important roles in antioxidant defense, nutrient metabolism, and regulation of cellular events (including gene expression, DNA and protein synthesis, cell proliferation and apoptosis, signal transduction, cytokine production and immune response, and protein glutathionylation). Glutathione deficiency contributes to oxidative stress, which plays a key role in aging and the pathogenesis of many diseases (including kwashiorkor, seizure, Alzheimer's disease, Parkinson's disease, liver disease, cystic fibrosis, sickle cell anemia, HIV, AIDS, cancer, heart attack, stroke, and diabetes).
CONCLUSIONS:
New knowledge of the nutritional regulation of GSH metabolism is critical for the development of effective strategies to improve health and to treat these diseases.

Structure Identification
Food Chemistry,2000,68(4):475-80.

Automated HPLC analysis of glutathione and thiol-containing compounds in grape juice and wine using pre-column derivatization with fluorescence detection.[Reference: WebLink]


METHODS AND RESULTS:
An easy and sensitive method for the analysis of Glutathione (GSH) and other thiol-containing compounds in grape juice and wine has been developed and optimized. Following a pre-column derivatization of thiols with o-phthalaldehyde (OPA) and 2 aminoethanol, isoindole derivatives are separated on reversed-phase HPLC column and quantified by a fluorescence detector. The minimum detection limits for thiols are: GSH, 3.3 nmol/l (1 g/l); cysteine, 22 mol/l (2.7 mg/L); methanethiol, 0.27 mol/l (12.8 g/l); ethanethiol, 0.65 mol/l (11 g/l). The method yields linear responses up to 40 and 21 mg/l for GSH and cysteine, respectively. GSH levels in two varietal grape juices during fermentation varied from 0 (starting juice) to 2.1 mg/l (wine) in Sauvignon blanc, while the GSH in a Palomino sample with 1.28 mg/l in the juice increased to 5.1 mg/l in the wine.
CONCLUSIONS:
This automated pre-column derivatization of thiols followed by an automatic injection procedure is sensitive, reproducible and rapid, with a run time of 35 min.

L-Glutathione Reduced Dilution Calculator

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L-Glutathione Reduced Molarity Calculator

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Preparing Stock Solutions of L-Glutathione Reduced

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.2539 mL 16.2697 mL 32.5394 mL 65.0787 mL 81.3484 mL
5 mM 0.6508 mL 3.2539 mL 6.5079 mL 13.0157 mL 16.2697 mL
10 mM 0.3254 mL 1.627 mL 3.2539 mL 6.5079 mL 8.1348 mL
50 mM 0.0651 mL 0.3254 mL 0.6508 mL 1.3016 mL 1.627 mL
100 mM 0.0325 mL 0.1627 mL 0.3254 mL 0.6508 mL 0.8135 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on L-Glutathione Reduced

Glutathione metabolism and its implications for health.[Pubmed:14988435]

J Nutr. 2004 Mar;134(3):489-92.

Glutathione (gamma-glutamyl-cysteinyl-glycine; GSH) is the most abundant low-molecular-weight thiol, and GSH/glutathione disulfide is the major redox couple in animal cells. The synthesis of GSH from glutamate, cysteine, and glycine is catalyzed sequentially by two cytosolic enzymes, gamma-glutamylcysteine synthetase and GSH synthetase. Compelling evidence shows that GSH synthesis is regulated primarily by gamma-glutamylcysteine synthetase activity, cysteine availability, and GSH feedback inhibition. Animal and human studies demonstrate that adequate protein nutrition is crucial for the maintenance of GSH homeostasis. In addition, enteral or parenteral cystine, methionine, N-acetyl-cysteine, and L-2-oxothiazolidine-4-carboxylate are effective precursors of cysteine for tissue GSH synthesis. Glutathione plays important roles in antioxidant defense, nutrient metabolism, and regulation of cellular events (including gene expression, DNA and protein synthesis, cell proliferation and apoptosis, signal transduction, cytokine production and immune response, and protein glutathionylation). Glutathione deficiency contributes to oxidative stress, which plays a key role in aging and the pathogenesis of many diseases (including kwashiorkor, seizure, Alzheimer's disease, Parkinson's disease, liver disease, cystic fibrosis, sickle cell anemia, HIV, AIDS, cancer, heart attack, stroke, and diabetes). New knowledge of the nutritional regulation of GSH metabolism is critical for the development of effective strategies to improve health and to treat these diseases.

The antioxidant role of glutathione and N-acetyl-cysteine supplements and exercise-induced oxidative stress.[Pubmed:18500954]

J Int Soc Sports Nutr. 2005 Dec 9;2:38-44.

An increase in exercise intensity is one of the many ways in which oxidative stress and free radical production has been shown to increase inside our cells. Effective regulation of the cellular balance between oxidation and antioxidation is important when considering cellular function and DNA integrity as well as the signal transduction of gene expression. Many pathological states, such as cancer, Parkinson's disease, and Alzheimer's disease have been shown to be related to the redox state of cells. In an attempt to minimize the onset of oxidative stress, supplementation with various known antioxidants has been suggested. Glutathione and N-acetyl-cysteine (NAC) are antioxidants which are quite popular for their ability to minimize oxidative stress and the downstream negative effects thought to be associated with oxidative stress. Glutathione is largely known to minimize the lipid peroxidation of cellular membranes and other such targets that is known to occur with oxidative stress. N-acetyl-cysteine is a by-product of glutathione and is popular due to its cysteine residues and the role it has on glutathione maintenance and metabolism. The process of oxidative stress is a complicated, inter-twined series of events which quite possibly is related to many other cellular processes. Exercise enthusiasts and researchers have become interested in recent years to identify any means to help minimize the detrimental effects of oxidative stress that are commonly associated with intense and unaccustomed exercise. It is possible that a decrease in the amount of oxidative stress a cell is exposed to could increase health and performance.

Glutathione homeostasis in response to exercise training and nutritional supplements.[Pubmed:10448900]

Mol Cell Biochem. 1999 Jun;196(1-2):31-42.

Glutathione plays a central role in the maintenance of tissue antioxidant defenses and in the regulation of redox sensitive signal transduction. In muscle cells, the level and redox status of GSH regulates activity of the redox sensitive transcription factor NF-kappaB. Physical exercise may cause oxidation of GSH in tissues such as the blood, skeletal muscle and liver. Endurance training strengthened GSH dependent tissue antioxidant defenses in most studies. Although studies investigating the effect of sprint training are few, current results show that sprint training may also have a beneficial effect on tissue GSH homeostasis. Skeletal muscle GSH level appears to be tightly regulated by the state of physical activity. Regular exercise enhances and chronic inactivity decreases the level of GSH in this tissue. N-acetyl-L-cysteine (NAC) and alpha-lipoic acid (LA) are two antioxidant dietary supplements that are able to enhance cellular GSH levels. Because LA can be recycled to its potent dithiol form, dihydrolipoate, by enzymes present in the human cell it has a clear advantage over NAC. Recently an improved form of LA, a positively charged analogue (LA-Plus), has been discovered. LA-Plus has more potent immuno-modulatory activity compared to LA. Both LA and NAC have been shown to have beneficial effects in protecting tissue GSH homeostasis against exercise induced oxidative stress.

Description

L-Glutathione reduced (GSH; γ-L-Glutamyl-L-cysteinyl-glycine) is an endogenous antioxidant and is capable of scavenging oxygen-derived free radicals.

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