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Merck

PHR1359

Supelco

L-Glutatión reducido

Pharmaceutical Secondary Standard; Certified Reference Material

Sinónimos:

γ-L-glutamil-L-cisteinil-glicina, GSH

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About This Item

Fórmula lineal:
H2NCH(CO2H)CH2CH2CONHCH(CH2SH)CONHCH2CO2H
Número de CAS:
Peso molecular:
307.32
Beilstein/REAXYS Number:
1729812
EC Number:
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:
NACRES:
NA.24

grade

certified reference material
pharmaceutical secondary standard

Quality Level

agency

traceable to Ph. Eur. Y0000517
traceable to USP 1294820

API family

glutathione

CofA

current certificate can be downloaded

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

mp

192-195 °C (dec.) (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-30°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 the most important nonprotein thiol widely distributed in animal tissues, plants, and microorganisms. GSH is also a key determinant of redox signaling and protection against oxidative stress.
Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

Application

These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.
Puede utilizarse a 5-10 mM para eluir la glutatión S-transferasa (GST) a partir de glutatión agarosa.

Biochem/physiol Actions

Antioxidante endógeno que desempeña un papel importante en la reducción de las especies de oxígeno reactivo formadas durante el metabolismo celular y el estallido respiratorio. La glutatión-S-transferasa cataliza la formación de tioéteres de glutatión con xenobióticos, leucotrienos y otras moléculas que tienen un centro electrofílico. El glutatión también forma enlaces de disulfuro con restos de cisteína de las proteínas. A través de estos mecanismos, puede tener el efecto paradójico de reducir la eficacia de los antineoplásicos.

Analysis Note

These secondary standards offer multi-traceability to the USP, EP (PhEur) and BP primary standards, where they are available.

Other Notes

This Certified Reference Material (CRM) is produced and certified in accordance with ISO 17034 and ISO/IEC 17025. All information regarding the use of this CRM can be found on the certificate of analysis.

Footnote

To see an example of a Certificate of Analysis for this material enter LRAA7940 in the slot below. This is an example certificate only and may not be the lot that you receive.

Recommended products

Find a digital Reference Material for this product available on our online platform ChemisTwin® for NMR. You can use this digital equivalent on ChemisTwin® for your sample identity confirmation and compound quantification (with digital external standard). An NMR spectrum of this substance can be viewed and an online comparison against your sample can be performed with a few mouseclicks. Learn more here and start your free trial.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable


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Certificados de análisis (COA)

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Visite la Librería de documentos

Glutathione: an overview of biosynthesis and modulation
Anderson ME
Chemico-Biological Interactions, 111, 1-14 (1998)
The glutathione status of cells
International Review of Cytology, 54, 109-160 (1978)
Dalia Gritenaite et al.
Genes & development, 28(14), 1604-1619 (2014-07-18)
A key function of the cellular DNA damage response is to facilitate the bypass of replication fork-stalling DNA lesions. Template switch reactions allow such a bypass and involve the formation of DNA joint molecules (JMs) between sister chromatids. These JMs
Karen Shahbabian et al.
Nucleic acids research, 42(13), 8692-8704 (2014-07-12)
Messenger RNA (mRNA) localization is coupled to the translational repression of transcripts during their transport. It is still unknown if this coupling depends on physical interactions between translational control and mRNA localization machineries, and how these interactions are established at
Julien Viaud et al.
Nature communications, 5, 4080-4080 (2014-06-07)
PtdIns5P is a lipid messenger acting as a stress-response mediator in the nucleus, and known to maintain cell activation through traffic alterations upon bacterial infection. Here, we show that PtdIns5P regulates actin dynamics and invasion via recruitment and activation of

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