108646-71-5

Basic information

• Product Name: AC-MET(O)-OH
• Synonyms: ACETYL-L-METHIONINE SULFOXIDE;AC-MET(O)-OH;AC-METHIONINE(O)-OH;N-Acetyl-L-methionine sulfoxide;(2S)-2-(Acetylamino)-4-(methylsulfinyl)butanoic acid;Acetyl-L-methionine sulfoxide≥ 95% (Assay);Ac-L-Met(O)-OH
• CAS NO: 108646-71-5
• Molecular Formula: C7H13NO4S
• Molecular Weight: 207.25
• Mol File: 108646-71-5.mol

Chemical Properties

• Melting Point: 181-183 °C
• Boiling Point: 587.3±45.0 °C(Predicted)
• Appearance: /
• Density: 1.341±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 3.41±0.10(Predicted)
• CAS DataBase Reference: AC-MET(O)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: AC-MET(O)-OH(108646-71-5)
• EPA Substance Registry System: AC-MET(O)-OH(108646-71-5)

Safety Data

• Hazardous Substances Data: 108646-71-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
AC-MET(O)-OH is used as an analyte for the development of stereospecific mechanism-based fluorescent sensors. These sensors are crucial in the biological study of methionine sulfoxide, which is an important molecule in various cellular processes, including protein function and regulation.
Used in Research and Development:
In the field of research and development, AC-MET(O)-OH is used as a key compound in the study of methionine sulfoxide and its role in cellular processes. This knowledge can be applied to develop new drugs and therapies targeting methionine sulfoxide-related pathways, potentially leading to breakthroughs in the treatment of various diseases.
Used in Quality Control and Analysis:
AC-MET(O)-OH can be employed in the quality control and analysis of pharmaceutical products, ensuring the presence and concentration of methionine sulfoxide in the desired range. This helps maintain the efficacy and safety of the products, as well as meeting regulatory requirements.
Used in Diagnostic Applications:
The compound can also be used in the development of diagnostic tools and tests that detect and measure methionine sulfoxide levels in biological samples. This can be particularly useful in the early detection and monitoring of diseases associated with altered methionine sulfoxide metabolism.

Upstream product

• 1115-47-5 N-acetyl-DL-methionine 
• 65-82-7 N-acetyl-l-methionine 
• 3226-65-1 L-methionine sulfoxide 
• 108-24-7 acetic anhydride 

Downstream Products

• 3226-65-1 L-methionine sulfoxide 

Relevant articles and documents

Efficient Metal-Free Aerobic Photooxidation of Sulfides to Sulfoxides Mediated by a Vitamin B2Derivative and Visible Light

We have developed a metal-free process for the aerobic photooxygenation of sulfides to sulfoxides mediated by riboflavin tetraacetate or riboflavin (vitamin B2) photocatalysts and visible light (450 nm) in an acetonitrile-water (85:15 v/v) mixture. The optimised solvent system leads to both singlet-oxygen and electron-transfer pathways in photooxygenation, thus allowing oxidation of electron-poor and electron-rich thioanisoles, dialkyl sulfides and sterically hindered sulfides. Besides having a broad substrate scope, the method has very short reaction times and requires low catalyst loading (down to 0.1 mol%). These properties are due to the high photocatalyst stability and the extremely high quantum yields (1.3 for thioanisole oxygenation). Moreover, the method is chemoselective, producing only sulfoxides without overoxidation to sulfones. Taking into account the broad substrate scope, high selectivity and high efficiency, this method distinguishes itself from those previously reported. Other advantages include easy work-up of the reaction mixture, the availability and biodegradability of the photocatalysts and mild reaction conditions. We demonstrated, on a preparative scale, its practical application in the synthesis of the psychostimulant modafinil, in the selective oxidation of methionine derivatives, and in the detoxification of mustard gas. (Figure presented.).

Electrostatic immobilization of substrate and polyoxotungstate catalyst at the surface of micelles for enhanced reaction efficiency in water

Polyoxometalate (POM)-basedmicellar catalysts were prepared by assembling the Keggin tri-anion [PW12O40]3? and (L)-N-acetylmethioninate salts of Gemini surfactants inwater. Contrary to conventional catalytic systems, we propose a new approach in which the POM catalyst and the substrate to be oxidized ((L)-N-acetylmethioninate) are both localized at the surface of micelles by electrostatic interaction before the reaction. The high local concentration of reactants due to their confinement at the surface of micelles enhances the reaction kinetics. Catalyst recovery experiments showed that, after two cycles of reactions, the activity of the catalysts was not changed.

Oxyhalogen-sulfur chemistry: Kinetics and mechanism of oxidation of N-Acetyl-L-methionine by aqueous iodine and acidified iodate

The use of N-acetyl-l-methionine (NAM) as a bio-available source for methionine supplementation as well as its ability to reduce the toxicity of acetaminophen poisoning has been reported. Its interaction with the complex physiological matrix, however, has not been thoroughly investigated. This manuscript reports on the kinetics and mechanism of oxidation of NAM by acidic iodate and aqueous iodine. Oxidation of NAM proceeds by a two electron transfer process resulting in formation of a sole product: N-acetyl-l-methionine sulfoxide (NAMS≤O). Data from electrospray ionization mass spectrometry confirmed the product of oxidation as NAMS≤O. The stoichiometry of the reaction was deduced to be IO3- + 3NAM → I- + 3NAMS≤O. In excess iodate, the stoichiometry was deduced to be 2IO 3 + 5NAM+ 2H+ → I2+ 5NAMS≤O + H 2O. The reaction between aqueous iodine and NAM gave a 1:1 stoichiometric ratio: NAM + I2 + H2O → NAMS≤O + 2I- + H+. This reaction was relatively rapid when compared with that between NAM and iodate. It did, however, exhibit some auto-inhibitory effects through the formation of triiodide (I3-) which is a relatively inert electrophile when compared with aqueous iodine. A simple mechanism containing 11 reactions gave a reasonably good fit to the experimental data. CSIRO 2014.

Repairing oxidized proteins in the bacterial envelope using respiratory chain electrons

The reactive species of oxygen and chlorine damage cellular components, potentially leading to cell death. In proteins, the sulfur-containing amino acid methionine is converted to methionine sulfoxide, which can cause a loss of biological activity. To res

Enantioselective Transfer Hydrogenation of Ketones using a Rhodium Catalyst containing a Methionine Sulphoxide Ligand

An in situ rhodium catalyst containing N-acetyl-(S)-methionine (R,S)-sulphoxide, and using propan-2-ol as a source of hydrogen, effects enantioselective hydrogenation of alkyl aryl ketones with up to 75percent enantiomeric excess.

Synthesis method of (2S)-2-(acetamino)-4-(methylsulfinyl)butyric acid

The invention relates to a synthesis method of (2S)-2-(acetamino)-4-(methylsulfinyl)butyric acid and mainly aims to solve the technical problems of high cost, high pollution, numerous by-products andharm to mass production of the existing synthesis method. The method comprises the following steps: (1) dissolving solid L-methionine in a sodium carbonate aqueous solution, dropwise adding liquid acetic anhydride, stirring for reacting, filtering and washing unreacted acetic anhydride in filtrate by using a mixed solution of ethyl acetate and petroleum ether, adding an extraction agent which is ethyl acetate into a water phase, acidizing by using solid citric acid, layering, washing, drying and carrying out reduced-pressure distillation to obtain an intermediate which is Nalpha-acetyl-L-methionine; and (2) dissolving the intermediate which is Nalpha-acetyl-L-methionine in acetic acid, dropwise adding hydrogen peroxide with mass percentage concentration of 30%, stirring for reacting, concentrating an obtained product till the product is dry, adding alcohol and crystallizing to obtain the product which is (2S)-2-(acetamino)-4-(methylsulfinyl)butyric acid. The (2S)-2-(acetamino)-4-(methylsulfinyl) butyric acid is used as a raw material for synthesizing a polypeptide drug.

Electron transfer reactions of photochemically generated ruthenium(III)-polypyridyl complexes with methionines

The oxidation of methionine (Met) plays an important role during biological conditions of oxidative stress as well as for protein stability. Ruthenium(III)-polypyridyl complexes, [Ru(NN)3]3+, generated from the photochemical oxidation of the corresponding Ru(II) complexes with molecular oxygen, undergo a facile electron transfer reaction with Met to form methionine sulfoxide (MetO) as the final product. Interaction of [Ru(NN)3]3+ with methionine leads to the formation of >S+? and (>S∴S+ species as intermediates during the course of the reaction. The interesting spectral, kinetic, and mechanistic study of the electron transfer reaction of four substituted methionines with six [Ru(NN)3]3+ ions carried out in aqueous CH3CN (1:1, v/v) by a spectrophotometric technique shows that the reaction rate is susceptible to the nature of the ligand in [Ru(NN)3]3+ and the structure of methionine. The rate constants calculated by the application of Marcus semiclassical theory to these redox reactions are in close agreement with the experimental values.

Selective Aerobic Oxidation of Sulfides Using a Novel Palladium Complex as the Catalyst Precursor

The palladium complex t2H)(μ-PBut2)>2, on exposure to oxygen in THF, generates an active catalytic system for the selective oxidation of sulfides to sulfoxides in 30-83percent yields.The process is stereospecific in the case of (+)-biotin-sulfoxide 4-nitrophenyl ester.