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G4251

Sigma-Aldrich

L-Glutathione reduced

≥98.0%

Synonym(s):

Glutathione-SH, γ-L-Glutamyl-L-cysteinyl-glycine, GSH

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10 MG
333,00 kr
300 MG
342,00 kr
1 G
440,00 kr
5 G
704,00 kr
10 G
1 490,00 kr
25 G
3 310,00 kr
50 G
5 940,00 kr
100 G
11 170,00 kr
250 G
24 500,00 kr
500 G
40 980,00 kr

333,00 kr


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10 MG
333,00 kr
300 MG
342,00 kr
1 G
440,00 kr
5 G
704,00 kr
10 G
1 490,00 kr
25 G
3 310,00 kr
50 G
5 940,00 kr
100 G
11 170,00 kr
250 G
24 500,00 kr
500 G
40 980,00 kr

About This Item

Linear Formula:
H2NCH(CO2H)CH2CH2CONHCH(CH2SH)CONHCH2CO2H
CAS Number:
Molecular Weight:
307.32
Beilstein:
1729812
EC Number:
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.26

333,00 kr


Please contact Customer Service for Availability

Request a Bulk Order

Product Name

L-Glutathione reduced, ≥98.0%

Quality Level

Assay

≥98.0%

form

powder

color

white

mp

192-195 °C (dec.) (lit.)

solubility

water: 50 mg/mL, clear, colorless

application(s)

detection

functional group

amine
carboxylic acid
thiol

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.[1]

Application

L-Glutathione (GSH) reduced has been used in the elution buffer to elute GST (glutathione S-transferase)-fused proteins using glutathione-agarose beads.[2][3] It has been used to prepare a standard curve for GSH analyses.[4]
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.[1]
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.

Other Notes

For additional information on our range of Biochemicals, please complete this form.

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

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Certificates of Analysis (COA)

Lot/Batch Number

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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
Nitric oxide as an independent regulatory factor in regenerating rat liver.
Tuncyurek P, et al.
Acta Chirurgica Belgica, 106, 581-581 (2006)
Effects of N-acetylcysteine, oral glutathione (GSH) and a novel sublingual form of GSH on oxidative stress markers: A comparative crossover study
Schmitt B, et al.
Redox Biology, 6, 198-205 (2015)
Surface Plasmon Resonance (SPR) Analysis of Binding Interactions of Inner-Ear Proteins.
Drescher DG, et al.
Methods in Molecular Biology, 1427, 165-165 (2016)
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)

Articles

Amino Acid Codon Wheel for fast RNA translation. Find which amino acid is translated from your RNA sequence quickly and easily.

Cellular oxidative stress is countered by enzymatic scavengers and antioxidant modulators against reactive oxygen species damage.

Antioxidants protect biological systems from oxidative damage produced by oxygen-containing free radicals and from redoxactive transition metal ions such as iron, copper, and cadmium.

Questions

1–8 of 8 Questions  
  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

      Helpful?

  3. Can an aqueous solution of L-Glutathione be autoclaved?

    1 answer
    1. L-Glutathione Reduced aqueous solutions should not be autoclaved as the high temperature and pressure during autoclaving can degrade the compound. It is recommended to filter-sterilize the solution using a sterile filter with a pore size of 0.2 micrometers.

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  4. Is glutathione (reduced) safe to store at room temperature in the powder format? I mistakenly stored it at room temperature for ~ 1 month.

    1 answer
    1. This product is stored at 2-8°C but is stable for short periods at room temperature. The items ship at ambient temperature and are stable for up to 2 weeks without refrigeration. The stability of the material beyond 2 weeks has not been evaluated. The end user would have to determine the suitability for specific applications experimentally.

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  5. After reconstitution, what temperature should the L-glutathione reduced be stored at?

    1 answer
    1. The stability of the product in solution has not been determined. However, it is recommended to prepare solutions fresh for best results.

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

    1 answer
    1. 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).

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

    1 answer
    1. 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.

      Helpful?

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

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

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