15776-11-1

Usage

Uses

Used in Pharmaceutical Industry:
(S)-4-(2'-METHYLTHIOETHYL)OXAZOLIDINE-2,5-DIONE is used as a building block for the synthesis of various pharmaceuticals and bioactive compounds. Its unique structure and thioether group can contribute to the development of new drugs with improved efficacy and selectivity.
Used in Medicinal Chemistry Research:
(S)-4-(2'-METHYLTHIOETHYL)OXAZOLIDINE-2,5-DIONE serves as a valuable starting material for the exploration of novel chemical entities and the optimization of existing drug candidates. Its chiral nature and functional groups provide opportunities for further chemical modifications and the discovery of new therapeutic agents.
Used in Agrochemical Development:
(S)-4-(2'-METHYLTHIOETHYL)OXAZOLIDINE-2,5-DIONE has potential applications in the agrochemical industry, where it can be utilized as a precursor for the synthesis of bioactive compounds with pesticidal or herbicidal properties. Its unique chemical features may contribute to the development of more effective and environmentally friendly agrochemicals.
Used in Materials Science:
(S)-4-(2'-METHYLTHIOETHYL)OXAZOLIDINE-2,5-DIONE can be explored for its potential use in the development of new materials with specific properties, such as improved stability, reactivity, or selectivity. Its thioether group and chiral nature may offer novel opportunities for the creation of advanced materials in various fields, including catalysis, sensors, and polymers.

Upstream product

• 75-44-5 phosgene 
• 59-51-8 DL-methionine 
• 27844-10-6 TMS-DL-Met-OTMS 
• 30411-84-8 (RS)-N-carbamoylmethionine 
• 63-68-3 L-methionine 
• 503-38-8 trichloromethyl chloroformate 
• 1104620-21-4 N-phenoxycarbonyl-L-methionine 
• 67-66-3 chloroform 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 41442-22-2 L-methionine sodium salt 
• 16639-89-7 N-Methoxycarbonyl-L-methionine 

Downstream Products

• 36261-61-7 L-methionyl-L-asparagine 
• 36261-62-8 MQ 
• 129288-42-2 Fmoc-Met-NCA 

Relevant academic research and scientific papers

Liver-Target and Glucose-Responsive Polymersomes toward Mimicking Endogenous Insulin Secretion with Improved Hepatic Glucose Utilization

Oral insulin therapy that targets the liver and further mimics glucose-responsive secretion holds promise for correcting defects in glucose metabolism caused by peripheral delivery. This work describes the construction of polymersomes (Pep-PMS), which are composed of glucose-responsive polymers decorated with peptides that readily bind to the ganglioside-monosialic acid (GM1) receptor in the intestinal epithelium. Pep-PMS are efficiently transported across the intestinal epithelium through GM1-mediated transcytosis, leading to their abundant accumulation in the liver. Moreover, Pep-PMS can efficiently encapsulate insulin in euglycemia and release them in hyperglycemia. Under hyperglycemic conditions, the Pep-PMS dissociate to release the encapsulated insulin in response to glucose oxidase (GOx)-induced H2O2. Surprisingly, the postprandial blood glucose levels of diabetic rats treated with Pep-PMS can be maintained even after being challenged by glucose administration. Hepatic glucose uptake and glycogen production are also elevated after treating diabetic rats with Pep-PMS, which is similar to glucose utilization in normal rats. Oral delivery systems that target the liver and serve as a reservoir for glucose-responsive insulin secretion may improve the therapeutic effect in people with diabetes.

Supported oligomethionine sulfoxide and Ellman's reagent for cysteine bridges formation

A large number of bioactive peptides are cyclized through a disulfide bridge. This structural feature is very important for both bioactivity and stability. The oxidation of cysteine side chains is challenging not only to avoid intermolecular reaction leading to oligomers and oxidation of other residues but also to remove solvents and oxidant such as dimethyl sulfoxide. Supported reagents advantageously simplify the work-up of such disulfide bond formation, but may lead to a significant decrease in yield of the oxidized product. In this study, two resins working through different mechanisms were evaluated: Clear-Ox, a supported version of Ellman's reagent and Oxyfold, consisting in a series of oxidized methionine residues. The choice of the supported reagent is discussed on the light of reaction speed, side-products formation and yield considerations.

Preparation of multifunctional and multireactive polypeptides via methionine alkylation

We report the development of a new "click"-type reaction for polypeptide modification based on the chemoselective alkylation of thioether groups in methionine residues. The controlled synthesis of methionine polymers and their alkylation by a broad range of functional reagents to yield stable sulfonium derivatives are described. These "methionine click" functionalizations are compatible with deprotection of other functional groups, use an inexpensive, natural amino acid that is readily polymerized and requires no protecting groups, and allow the introduction of a diverse range of functionality and reactive groups onto polypeptides.

A new simple and quantitative synthesis of α-aminoacid-N-carboxyanhydrides (oxazolidines-2,5-dione)

Nitrosation of chiral N-carbamoylaminoacids with a mixture of NO and O2 gives, with the same configuration and in quantitative yield the corresponding α-aminoacid-N-carboxyanhydrides (NCA), well known precursors of peptides. The by products of this reaction are N2 and H2O. Copyright (C) 1996 Elsevier Science Ltd.

METHOD FOR PRODUCING AMINO ACID-N-CARBOXYLIC ACID ANHYDRIDE

PROBLEM TO BE SOLVED: To provide: a method for safely and efficiently producing amino acid-N-carboxylic acid anhydride; and a method for producing peptide by using the obtained amino acid-N-carboxylic acid anhydride. SOLUTION: The method for producing an amino acid-N-carboxylic acid anhydride according to the present invention is characterized in that the amino acid-N-carboxylic acid anhydride is represented by the following formula (II), and a step of irradiating a composition containing a halogenated methane and an amino acid compound represented by the following formula (I) with high energy light in the presence of oxygen is included. [In the formula, R1 represents an amino acid side chain group in which the reactive group is protected, and R2 represents H or the like.]. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

METHOD OF SYNTHESIZING N-CARBOXYANHYDRIDE USING FLOW REACTOR

PROBLEM TO BE SOLVED: To provide a synthesis method that allows high-yield continuous production of a compound of interest in synthesis and production of N-carboxyanhydride (NCA) and the like using a flow reactor. SOLUTION: In a synthesis method using a flow reactor 100, a basic solution adjusted in advance to a pH of 7-14 becomes acidic with a pH of 0-7, or an acidic solution adjusted in advance to a pH of 0-7 becomes basic with a pH of 7-14, within 60 seconds after the start of mixture of at least two ingredient solutions. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2020,JPOandINPIT

BIORESPONSIVE HYDROGEL MATRIXES AND METHODS OF USE

Disclosed are compositions and methods for treating cancer with a hydrogel matrix comprising a chemotherapeutic agent and a blockade inhibitor. Disclosed herein are bioresponsive hydrogel matrixes comprising a reactive oxygen species scavenger.

Influence of Sulfoxide Group Placement on Polypeptide Conformational Stability

The synthesis of a homologous series containing five new nonionic sulfoxide containing polypeptides was described. Sulfoxide groups bestowed water solubility for all homologues, which allowed their use as a model for study of helix-coil transitions in water while avoiding contributions from charged groups or phase separation. Polypeptides were found to adopt chain conformations in water that were dependent on distance of sulfoxides from chain backbones, overall side-chain lengths, and solvent. These results allow preparation of polypeptide segments with different chain conformations without changing chemical functionality for potential use in structural studies and functional applications.

Rapid and Mild Synthesis of Amino Acid N-Carboxy Anhydrides: Basic-to-Acidic Flash Switching in a Microflow Reactor

Polymerization of N-carboxy anhydrides (NCAs) is the primary process used to prepare polypeptides. The synthesis of various pure NCAs is key to the efficient synthesis of polypeptides. The only practical method that can be used to synthesize NCAs requires harsh acidic conditions that make acid-labile substrates unusable and results in an undesired ring opening of NCAs. Basic-to-acidic flash switching and subsequent flash dilution technology in a microflow reactor was used to demonstrate the synthesis of NCAs. It is both rapid (0.1 s) and mild (20 °C) and includes substrates containing acid-labile functional groups. The basic-to-acidic flash switching enabled both an acceleration of the desired NCA formation and avoided the undesired ring opening of NCAs. The flash dilution precluded the undesired decomposition of acid-labile functional groups. The developed process allowed the synthesis of various NCAs which cannot be readily synthesized using conventional batch methods.

Revolutionary phosgene-free synthesis of α-amino acid N-carboxyanhydrides using diphenyl carbonate based on activation of α-amino acids by converting into imidazolium salts

The phosgene-free synthesis of α-amino acid n-carboxyanhydrides using diphenyl carbonate based on activation of α-amino acids by converting into imidazolium salts was reported. 1-Ethyl-3-methylimidazolium bromide (4.77 g, 25.0 mmol) was dissolved in water (25 mL) and was passed through a column of Amberlite IRA 400 CL (50 cm3) using 250 mL of water as an eluent to synthesize amino acid imidazolium salt. A solution of L-phenylalanine imidazolium salt (550 mg, 2.0 mmol) in acetonitrile (15 mL) was added dropwise to a solution of diphenyl-carbonate (427 mg, 2.00 mmol) in acetonitrile (5 mL) at room temperature, and the reaction mixture was stirred at room temperature to synthesize urethane derivative. The results showed that all of the obtained imidazolium salts were soluble in chloroform, dichloromethane, 2-butanone acetonitrile, and not soluble in tetrahydrofuran.