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G4251

Sigma-Aldrich

L-Glutathione reduced

≥98.0%

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Synonym(s):
Glutathione-SH, γ-L-Glutamyl-L-cysteinyl-glycine, GSH
Linear Formula:
H2NCH(CO2H)CH2CH2CONHCH(CH2SH)CONHCH2CO2H
CAS Number:
70-18-8
Molecular Weight:
307.32
Beilstein:
1729812
EC Number:
200-725-4
MDL number:
MFCD00065939
PubChem Substance ID:
24895164
NACRES:
NA.26

Quality Level

300

Assay

≥98.0%

form

powder

color

white

mp

192-195 °C (dec.) (lit.)

application(s)

detection

storage temp.

2-8°C

SMILES string

N[C@@H](CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O)C(O)=O

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

InChI key

RWSXRVCMGQZWBV-WDSKDSINSA-N

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Amino Acid Sequence

γ-Glu-Cys-Gly

General description

Glutathione (GSH) is a ubiquitous molecule found in many cells and tissues. The three amino acids present in GSH are glycine, cysteine, and glutamic acid.

Application

L-Glutathione (GSH) reduced has been used in the elution buffer to elute GST (glutathione S-transferase)-fused proteins using glutathione-agarose beads. It has been used to prepare a standard curve for GSH analyses.
May be used at 5-10 mM to elute glutathione S-transferase (GST) from glutathione agarose.

Biochem/physiol Actions

Glutathione (GSH) forms conjugates with various metabolites and xenobiotics. It acts as an important co-factor for various enzymes. GSH is involved in many metabolic and signaling pathways. Glutathione functions as a thiol buffer for cellular proteins like thioredoxins and metallothioneins. GSH is also involved in the regeneration of antioxidants like tocopherols and ascorbate.
Endogenous antioxidant that plays a major role in reducing reactive oxygen species formed during cellular metabolism and the respiratory burst. Glutathione-S-transferase catalyzes the formation of glutathione thioethers with xenobiotics, leukotrienes, and other molecules that have an electrophilic center. Glutathione also forms disulfide bonds with cysteine residues in proteins. Via these mechanisms, it can have the paradoxical effect of reducing the efficacy of anti-cancer agents.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

常规特殊物品

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25G
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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

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  4. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  5. How do I solubilize Product G4251, L-Glutathione reduced?

    Reduced glutathione is freely soluble in water, dilute alcohol, liquid ammonia, and DMF.

  6. What is the solution stability of Product G4251, L-Glutathione reduced?

    Aqueous solutions readily oxidize in air to oxidized glutathione, GSSG.  Half-lives of reduced glutathione in solution at various pHs and temperatures have been reported.  The half-life of reduced glutathione is increased in the presence of a chelating agent.  For supporting references, please consult the product information sheet (under Documents, above).

  7. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Hee Woong Yang et al.
FEBS letters, 593(15), 2060-2068 (2019-06-11)
Ribosomal protein S3 (rpS3) has endonuclease activity for DNA repair. In particular, rpS3 cleaves the phosphodiester bonds of damaged DNA. In this study, we show that the repair domain of rpS3 spans amino acids 144-189. We fused rpS3 with the
Cu 2 O/NiO x/graphene oxide modified glassy carbon electrode for the enhanced electrochemical oxidation of reduced glutathione and nonenzyme glucose sensor.
Yuan B et al.
Electrochimica Acta, 104, 78-78 (2013)
Co-purification and direct interaction of Ras with caveolin, an integral membrane protein of caveolae microdomains. Detergent-free purification of caveolae microdomains.
Song KS, et al.
The Journal of Biological Chemistry, 271, 9690-9690 (1996)
Surface Plasmon Resonance (SPR) Analysis of Binding Interactions of Inner-Ear Proteins.
Drescher DG, et al.
Methods in Molecular Biology, 1427, 165-165 (2016)
Nitric oxide as an independent regulatory factor in regenerating rat liver.
Tuncyurek P, et al.
Acta Chirurgica Belgica, 106, 581-581 (2006)
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