S-Methylglutathione

• CAT Number: R060469
• CAS Number: 2922-56-7
• Molecular Formula: C11H19N3O6S
• Molecular Weight: 321.35
• Purity: ≥95%
• Synonyms: (2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-3-methylsulfanyl-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
• InChI: 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)/t6-,7-/m0/s1
• InChIKey: QTQDDTSVRVWHMO-BQBZGAKWSA-N
• SMILES: CSCC(C(=O)NCC(=O)O)NC(=O)CCC(C(=O)O)N

S-Methylglutathione is an S-substitued glutathione and a stronger nucleophile than GSH[1]. S-Methylglutathione has inhibitory effect on glyoxalase 1[2].
S-Methylglutathione (GS-Me) is a stronger nucleophile than GSH, which is rationalized by the more positive inductive effect of the methyl group[1].

Reference

[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.
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[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