S methyl l cysteine

Manufactured by Merck Group

Sourced in United States

S-methyl-l-cysteine is a laboratory chemical compound used in research and development applications. It is a sulfur-containing amino acid derivative. S-methyl-l-cysteine serves as a precursor and building block for various chemical reactions and analyses, but its core function is not interpreted or extrapolated on in this response.

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5 protocols using s methyl l cysteine

Selenium and Sulfur Amino Acid Derivatives

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l-Glutamine, l-methionine, l-selenomethionine (SM), S-methyl-l-cysteine (SMC), sodium α-keto-γ-methiolbutyrate (KMB; 4-methylthio-2-oxobutanoate), sodium α-ketoglutarate, β-mercaptoethanol, dithiothreitol (DTT), sodium dodecyl sulfate (SDS) and metaphosphoric acid (MPA) were obtained from Sigma-Aldrich (St. Louis, MO, USA). The α-keto acids derived from SM and SMC (i.e., α-keto-γ-methylselenobutyrate (KMSB) and β-methylselenopyruvate (MSP), respectively) were made in situ from the corresponding l-amino acids with snake venom l-amino acid oxidase [10 (link)]. 2,4-Dinitrophenylhydrazine was obtained from Kodak (Rochester, NY, USA). KGM was synthesized from l-glutamine with l-amino acid oxidase as described [11 (link)].

Dorai T., Dorai B., Pinto J.T., Grasso M, & Cooper A.J. (2019). High Levels of Glutaminase II Pathway Enzymes in Normal and Cancerous Prostate Suggest a Role in ‘Glutamine Addiction’. Biomolecules, 10(1), 2.

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Enzymatic Assay for Cysteine Derivatives

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S-methyl-L-cysteine and nicotinamide adenine dinucleotide reduced form (NADH) were obtained from Sigma-Aldrich (Schnelldorf, Germany). PLP and D,L-dithiothreitol (DTT) were purchased from Serva (Heidelberg, Germany). Propiin (S-propyl-L-cysteine sulfoxide), methiin (S-methyl-L-cysteine sulfoxide), and alliin (S-allyl-L-cysteine sulfoxide) were prepared according to [27 (link)]. GE Healthcare (Styria, Austria) provided ethylenediaminetetraacetic acid (EDTA). Penicillin was purchased from PanEco (Moscow, Russia). 2-Nitro-5-thiobenzoate (NTB) was prepared according to [28 (link)]. The plasmid with the gene of C. novyi C115H MGL was obtained from Eurogene (Moscow, Russia). Sigma-Aldrich (Schnelldorf, Germany) provided 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT). Trypan blue, phosphate-buffered saline (PBS) and dimethyl sulfoxide (DMSO) were purchased from PanEco (Moscow, Russia). Fetal bovine serum was obtained from HyClone (Logan, UT, USA) along with flasks and plates were purchased from Nunc (Moscow, Russia).

Abo Qoura L., Morozova E., Kulikova V., Karshieva S., Sokolova D., Koval V., Revtovich S., Demidkina T, & Pokrovsky V.S. (2022). Methionine γ-Lyase-Daidzein in Combination with S-Propyl-L-cysteine Sulfoxide as a Targeted Prodrug Enzyme System for Malignant Solid Tumor Xenografts. International Journal of Molecular Sciences, 23(19), 12048.

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Quantification of S-methyl-L-cysteine by LC-MS

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SMCSO (>94%) was purchased from LKT laboratories (St. Paul, MN, USA). S-methyl-l-cysteine (>98%), trichloroacetic acid (TCA) (>99%) and heptaflurobutyric acid (>99.5%) were purchased from Sigma^® (Gillingham, UK). All chemical solvents with high purity grade were used for LC-MS analysis: Ammonium acetate (>99%) was purchased from Fluka. Purified water was obtained from the Milli-Q^® Integral Water Purification System (Millipore Advantage, Watford, UK).

Sivapalan T., Melchini A., Coode-Bate J., Needs P.W., Mithen R.F, & Saha S. (2019). An LC-MS/MS Method to Measure S-Methyl-l-Cysteine and S-Methyl-l-Cysteine Sulfoxide in Human Specimens Using Isotope Labelled Internal Standards. Molecules, 24(13), 2427.

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Amino Acid Derivatization in HCl

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Solutions of 50 mg ml⁻¹ of l-methionine (Sigma Aldrich; M9625) and S-methyl-l-cysteine (Sigma; M6626) were prepared in 1 M HCl and passed through a 0.2-μm filter. Five hundred microliters of each solution (25 mg of each compound) was added to a serum vial, and the liquid was evaporated with a stream of nitrogen gas at 50°C. The amino acids were then derivatized as described above. A glass syringe was used to add 25 to 50 μl of methyl acetate to dilute the resulting oils.

Wirth J.S., Wang T., Huang Q., White R.H, & Whitman W.B. (2020). Dimethylsulfoniopropionate Sulfur and Methyl Carbon Assimilation in Ruegeria Species. mBio, 11(2), e00329-20.

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Evaluating β-Lyase Activity in Yeast

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β-Lyase activity was evaluated on a medium containing the following: 0.1% S-methyl-L-cysteine (Sigma-Aldrich), 0.01% pyridoxal-5′-phosphate (Sigma-Aldrich), 1.2% Yeast Carbon Base (Difco, Detroit, MI, USA) and 2% agar. This medium was adjusted to pH 3.5 and sterilized as described above to avoid agar hydrolysis. The agar solution was autoclaved, and all the other components were adjusted to pH 3.5 with HCl and filtered (0.22 μm), then both fractions were mixed when the agar solution was around 60°C. Any significant growth of the colonies after 48–72 h indicated the presence of β-lyase activity (Patent pending). T. delbrueckii CECT 10676 and R. glutinis CECT 10143 were used as positive and negative controls, respectively.

Belda I., Ruiz J., Alastruey-Izquierdo A., Navascués E., Marquina D, & Santos A. (2016). Unraveling the Enzymatic Basis of Wine “Flavorome”: A Phylo-Functional Study of Wine Related Yeast Species. Frontiers in Microbiology, 7, 12.

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