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M4139

Sigma-Aldrich

S-Methylglutathione

>98% (TLC), suitable for cell culture

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Synonym(s):
L-γ-glutamyl-S-methyl-L-cysteinyl-glycine
Empirical Formula (Hill Notation):
C11H19N3O6S
CAS Number:
2922-56-7
Molecular Weight:
321.35
MDL number:
MFCD00056730
UNSPSC Code:
12352200
PubChem Substance ID:
24896906
NACRES:
NA.26

assay

>98% (TLC)

Quality Level

200

form

powder

technique(s)

cell culture | mammalian: suitable

color

white

storage temp.

2-8°C

SMILES string

CSCC(NC(=O)CCC(N)C(O)=O)C(=O)NCC(O)=O

InChI

1S/C11H19N3O6S/c1-21-5-7(10(18)13-4-9(16)17)14-8(15)3-2-6(12)11(19)20/h6-7H,2-5,12H2,1H3,(H,13,18)(H,14,15)(H,16,17)(H,19,20)

InChI key

QTQDDTSVRVWHMO-UHFFFAOYSA-N

Related Categories

Biochem/physiol Actions

S-methylglutathione is a methionine containing peptide and glyoxylase inhibitor.

Substrates

Useful as a glyoxylase inhibitor.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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L-Glutathione reduced ≥98.0%

Sigma-Aldrich

G4251

L-Glutathione reduced

Michel Cailleret et al.
Circulation, 109(3), 406-411 (2004-01-21)
The negative effect of tumor necrosis factor-alpha (TNF-alpha) on heart contraction, which is mediated by sphingosine, is a major component in heart failure. Because the cellular level of glutathione may limit sphingosine production via the inhibition of the Mg-dependent neutral
J D Piganelli et al.
Diabetes, 47(8), 1212-1218 (1998-08-14)
IDDM results from the destruction of pancreatic beta-cells by autoreactive T-cells that appear to avoid deletion early in development, possibly due to improper interaction with antigen-presenting cells (APCs) resident in the thymus or periphery. In the nonobese diabetic (NOD) mouse
Piotr Filipiak et al.
The journal of physical chemistry. B, 117(8), 2359-2368 (2013-01-26)
Nanosecond laser flash photolysis was used to generate sulfur radical cations of the thioether, S-methylglutathione (S-Me-Glu), via the one-electron oxidation of this thioether by triplet 4-carboxybenzophenone. The purpose of this investigation was to follow the neighboring group effects resulting from
C Sherrill et al.
Journal of bacteriology, 180(6), 1454-1459 (1998-03-27)
Glutathione (gamma-GluCysGly, GSH) is not found in most gram-positive bacteria, but some appear to synthesize it and others, including Streptococcus mutans ATCC 33402, import it from their growth medium. Import of oxidized glutathione (GSSG) by S. mutans 33402 in 7H9
Alice Rothnie et al.
Molecular pharmacology, 74(6), 1630-1640 (2008-09-05)
Multidrug resistance protein 1 (MRP1/ABCC1) is an ATP-dependent polytopic membrane protein that transports many anticancer drugs and organic anions. Its transport mechanism is multifaceted, especially with respect to the participation of GSH. For example, vincristine is cotransported with GSH, estrone
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