S-Methyl glutathione

Names

[ Name ]:
S-Methyl glutathione

[Synonym ]:
(2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-3-methylsulfanyl-1-oxopropan-2-yl]amino]-5-oxopentanoic acid

Biological Activity

[Description]:

S-Methylglutathione is an S-substitued glutathione and a stronger nucleophile than GSH[1]. S-Methylglutathione has inhibitory effect on glyoxalase 1[2].

[Related Catalog]:

Research Areas >> Others

Signaling Pathways >> Others >> Others

[In Vitro]

S-Methylglutathione (GS-Me) is a stronger nucleophile than GSH, which is rationalized by the more positive inductive effect of the methyl group[1].

[References]

[1]. Foye WO, et al. Synthesis and evaluation of N-alkanoyl-S-benzyl-L-cysteinylglutamic acid esters as glyoxalase I inhibitors and anticancer agents. J Pharm Sci. 1984 Apr;73(4):559-61.

[2]. Milos I. Djuran,et al. Reactivity of chloro- and aqua(diethylenetriamine)platinum(II) ions with glutathione, S-methylglutathione, and guanosine 5'-monophosphate in relation to the antitumor activity and toxicity of platinum complexes. Inorg. Chem. 1991, 30, 12, 2648–2652

Chemical & Physical Properties

[ Molecular Formula ]:
C₁₁H₁₉N₃O₆S

[ Molecular Weight ]:
321.35000

[ Exact Mass ]:
321.09900

[ PSA ]:
191.10000

[ LogP ]:
0.60800

[ Vapour Pressure ]:
1.23E-25mmHg at 25°C

[ Storage condition ]:
2~8°C

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3.0

[ HS Code ]:
2930909090

Customs

[ HS Code ]: 2930909090

[ Summary ]:
2930909090. other organo-sulphur compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles

Crystallographic and thermodynamic analysis of the binding of S-octylglutathione to the Tyr 7 to Phe mutant of glutathione S-transferase from Schistosoma japonicum.

Biochemistry 44 , 1174-1183, (2005)

Glutathione S-transferases are a family of multifunctional enzymes involved in the metabolism of drugs and xenobiotics. Two tyrosine residues, Tyr 7 and Tyr 111, in the active site of the enzyme play ...

Calcium-sensing receptor-dependent activation of CREB phosphorylation in HEK293 cells and human parathyroid cells.

Am. J. Physiol. Endocrinol. Metab. 304(10) , E1097-104, (2013)

In addition to its acute effects on hormone secretion, epithelial transport, and shape change, the calcium-sensing receptor (CaSR) modulates the expression of genes that control cell survival, prolife...

3-Methyleneoxindole: an affinity label of glutathione S-transferase pi which targets tryptophan 38.

Biochemistry 40(25) , 7549-58, (2001)

The compound 3-methyleneoxindole (MOI), a photooxidation product of the plant auxin indole-3-acetic acid, functions as an affinity label of the dimeric pi class glutathione S-transferase (GST) isolate...