7728-98-5

Usage

Uses

Used in Pharmaceutical Industry:
S-methylcysteine is used as a therapeutic agent for its potential health benefits, including its antioxidant and anti-inflammatory properties. It is being researched for its protective effects on the liver and support for cardiovascular health.
Used in Anticancer Applications:
S-methylcysteine is used as an anti-cancer agent due to its potential to inhibit the growth of tumor cells. It is being investigated for its role in cancer treatment and prevention.
Used in Nutraceutical Industry:
S-methylcysteine is used as a dietary supplement for its potential health benefits, including its antioxidant and anti-inflammatory properties, as well as its protective effects on the liver and support for cardiovascular health.

InChI:InChI=1/C4H9NO2S/c1-8-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)

Upstream product

• 52-90-4 L-Cysteine 
• 18412-81-2 dodecyl-dimethylsulphonium iodide 
• 74-93-1 methylthiol 
• 56-45-1 L-serin 
• 3981-36-0 3-chloro-DL-alanine 
• 21593-77-1 S-allyl cysteine 
• 16637-59-5 (2R)-2-acetylamino-3-methylthiopropionic acid 
• 7664-41-7 ammonia 
• 74-88-4 methyl iodide 
• 77-78-1 dimethyl sulfate 
• 616-38-6 carbonic acid dimethyl ester 
• 67-56-1 methanol 
• 52-89-1 l-cysteine hydrochloride 
• 1187-84-4 S-methyl-L-cysteine 

Downstream Products

• 87123-05-5 N-(2-benzylthio-2-methylpropanoyl)-S-methyl-L-cysteine 
• 66255-16-1 s-methyl-s-cysteine 
• 792132-38-8 Methionin-ethylester 
• 16637-59-5 (2R)-2-acetylamino-3-methylthiopropionic acid 
• 99855-84-2 N-benzoyl-S-methyl-L-cysteine 
• 81251-82-3 N-(2,4-dinitro-phenyl)-S-methyl-L-cysteine 

Relevant academic research and scientific papers

Direct monitoring of biocatalytic deacetylation of amino acid substrates by1H NMR reveals fine details of substrate specificity

Amino acids are key synthetic building blocks that can be prepared in an enantiopure form by biocatalytic methods. We show that thel-selective ornithine deacetylase ArgE catalyses hydrolysis of a wide-range ofN-acyl-amino acid substrates. This activity was revealed by1H NMR spectroscopy that monitored the appearance of the well resolved signal of the acetate product. Furthermore, the assay was used to probe the subtle structural selectivity of the biocatalyst using a substrate that could adopt different rotameric conformations.

Asymmetric synthesis of (S,R)- and (R,R)-methiin stereoisomers

An asymmetric synthesis of (+)- and (–)-methiine (S-methyl-(R)-cysteine sulfoxide) diastereomers has been developed. These natural sulfur compounds were isolated from a variety of Brassica vegetables. As the starting compound, (R)-cysteine was used, which was methylated to form (R)-S-methylcysteine. Then the oxidation of S-methylcysteine with tert-butyl hydroperoxide catalyzed by the chiral tetra(isopropylate)titanium/(S)- or (R)-Binol complex led to the formation of (1 R,2S)-(+)- or (1 R,2R)-(–)-methiin stereomers.

Symmetric benzidine derivatives as anti-HCV agents: Insight into the nature, stereochemistry of the capping amino acid and the size of the terminal capping carbamates

Novel symmetric molecules, bearing a benzidine prolinamide core, two terminal carbamate caps of variable sizes and nature, including natural and unnatural amino acids were developed. Several terminal N-carbamate substituents of the core structure, ranging from linear methyl, ethyl and butyl groups to branching isobutyl group; and an aromatic substituent were also synthesized. Series 1 has hydrophobic AA residues, namely S and R phenylglycine and a terminal carbamate capping group, whereas Series 2 bears sulphur containing amino acids, specifically S and R methionine and the natural R methylcysteine. The novel compounds were tested for their inhibitory activity (EC50) and their cytotoxicity (CC50), using an HCV 1b (Con1) reporter replicon cell line. Compound 4 with the unnatural capping residue, bearing D-Phenylglycine amino acid residue and N-isobutyloxycarbonyl capping group, was the most active within the two series, with EC50 = 0.0067 nM. Moreover, it showed high SI50 > 14788524 and was not cytotoxic at the highest tested concentration (100 μΜ), indicating its safety profile. Compound 4 also inhibited HCV genotypes 2a, 3a and 4a. Compared to the clinically approved NS5A inhibitor Daclatasvir, compound 4 shows higher activity against genotypes 1b and 3a, as well as improved safety profile.

Composition for promoting differentiation of skin keratinocyte comprising a SAC derivatives or a SMC derivatives

The present invention relates to a composition for promoting keratinocyte differentiation. More specifically, SAC derivative or SMC derivatives as an active ingredient promotes differentiation of keratinocytes to promote skin keratinocyte differentiation, has excellent anti-wrinkling effect, skin barrier recovery effect, and is applicable to pharmaceutical, cosmetic, soap, body, shampoo and pack.

KCNT1 INHIBITORS AND METHODS OF USE

The present invention is directed to, in part, compounds and compositions useful for preventing and/or treating a neurological disease or disorder, a disease or condition relating to excessive neuronal excitability, and/or a gain-of-function mutation in a gene (e.g., KCNT1). Methods of treating a neurological disease or disorder, a disease or condition relating to excessive neuronal excitability, and/or a gain-of-function mutation in a gene such as KCNT1 are also provided herein.

Discovery of a novel dipeptidyl boronic acid proteasome inhibitor for the treatment of multiple myeloma and triple-negative breast cancer

A series of novel dipeptidyl boronic acid compounds were designed, synthesized and biologically investigated for the inhibition of the β5 subunit of 20S proteasome and several compounds showed high activities with IC50 values of less than 10 nM. Some of these compounds potently inhibited the multiple myeloma (MM) cancer cell lines with IC50 values of less than 10 nM. It was reported that the inhibition of both β2 and β5 subunits strongly increased the cytotoxicity of proteasome inhibitors in solid tumor cells, so some of the compounds were evaluated for the inhibition of the β2 subunit and the solid tumor triple-negative breast cancer cell line MDA-MB-231. The results showed that three compounds were active for both the β2 subunit and the triple-negative breast cancer cell line MDA-MB-231. The in vivo pharmacokinetic results showed that compound 8t had good biological parameters for both ig and iv administrations. An in vivo pharmacodynamic experiment showed that compound 8t inhibited the β5 subunit in whole blood more greatly than the marketed MLN9708 with the same dose at different time periods. A pathological analysis indicated that the injection of compound 8t in the tumor of a triple-negative breast cancer xenograft mice model led to tumor cell necrosis, nucleus condensation, deep staining, cell fragmentation, dissolution and neutrophil infiltration compared with the control group. The data in hand showed that compound 8t might be an effective candidate for the treatment of both MM and triple-negative breast cancer.

Synthesis and application of peptide borate compounds

The invention belongs to the field of drug synthesis, and specifically relates to a series of novel peptide borate compounds or pharmaceutical salts thereof, and a preparation method and pharmaceutical application thereof. The structure of the peptide borate compounds or the pharmaceutical salts thereof is as shown in a formula I which is described in the specification. The compounds of the invention can be used for preparing proteasome inhibitors, and thus can be further used for treating solid tumors and blood tumors.

Engineered Citrobacter freundii methionine γ-lyase effectively produces antimicrobial thiosulfinates

Antimicrobial activity of thiosulfinates in situ produced by mixtures of Citrobacter freundii methionine γ-lyase (MGL) with new substrates, L-methionine and S-(alkyl/allyl)-L-cysteine sulfoxides has been recently demonstrated (Anufrieva et?al., 2015). This opens a way to the rational design of a new biotechnologically relevant antimicrobial drug producer. To increase the efficiency of the enzyme toward sulfoxides, the mutant forms of MGL, with the replacements of active site cysteine 115 with alanine (C115A MGL) and histidine (C115H MGL) were obtained. The replacement of cysteine 115 by histidine results in the loss of activity of the mutant enzyme in the γ-elimination reaction of physiological substrate, whereas the activity in the β-elimination reaction of characteristic substrates persists. However, the catalytic efficiency of C115H MGL in the β-elimination reaction of S-substituted L-cysteine sulfoxides is increased by about an order of magnitude compared to the wild type MGL. The antibacterial activity of C115H MGL mixtures with a number of sulfoxides was assessed against Gram-positive and Gram-negative bacteria. The bacteriostatic effect was more pronounced against Gram-positive than against Gram-negative bacteria, while antibacterial potential proved to be quite similar. Thus, the mutant enzyme C115H MGL is an effective catalyst, in particular, for decomposition of sulfoxides and the pharmacological couples of the mutant form with sulfoxides might be new antimicrobial agents.

Dipeptide boric acid composed of carboxylic acid and alpha-amino acid as well as ester compound thereof, and preparation method and application of dipeptide boric acid and ester compound thereof

The invention belongs to the field of drug synthesis and in particular relates to a series of novel peptide boric acids as well as an ester compound or pharmaceutical salt thereof, and a preparation method and application of the peptide boric acids as well as the ester compound or pharmaceutical salt thereof in pharmacodynamics. A structure of the peptide boric acid and the ester compound or pharmaceutical salt thereof is shown in a formula I (described in the specification). The compound provided by the invention can be used for preparing a proteasome inhibitor and can further be used for treating solid tumours and blood tumours, wherein the solid tumours are selected from non-small cell lung cancer, small cell lung cancer, lung adenocarcinoma, lung squamous carcinoma, pancreatic cancer, breast cancer, prostate cancer, liver cancer, skin cancer, epithelial cell cancer, gastrointestinal stromal tumor, nasopharynx cancer and leukemia; and the blood tumours are selected from multiple myeloma, mantle cell lymphoma and histiocytic lymphoma.

A step-by-step crystallization for preparing thio alkyl/alkenyl cysteine sulfoxide method

The invention discloses a method for preparing thioalkyl/alkenyl cysteine sulfoxide by fractional crystallization, belonging to the technical field of compound preparation. The method comprises the following steps: adding cysteine or cysteine salts, a sodium hydroxide solution and an R group (alkyl or alkenyl)-derived material into absolute ethanol in sequence for reaction to synthesize coarse ACSs, re-crystallizing ACSs, purifying, oxidizing to form ACSOs, and fractionally crystallizing to obtain natural dextrorotatory ACSOs, wherein the R group-derived material is replaced to synthesize different types of ACSOs in allium; enantiomers in racemes are separated by adopting the fractional crystallization method to obtain natural dextrorotatory ACSOs with optical activity. Compared with a conventional extraction method, the method has the characteristics that the yield and the purity are high, a conventional complicated extraction process is avoided, the product has the optical activity, and the physical property is close to that of natural extract; the product is used in the fields of health products, pharmaceuticals and the like, the effects of resisting bacteria and cancers, reducing blood fat and the like of ACSOs are brought into play, or the product serves as an intermediate such as an active ingredient-diallyl thiosulfinate for synthesizing allium.