3493-11-6

Usage

Uses

Used in Organic Synthesis:
L-METHIONINE METHYLSULFONIUM IODIDE is used as a reagent for its ability to act as a methyl donor in various chemical reactions, facilitating the synthesis of a wide range of organic compounds.
Used in Biochemical Research:
L-METHIONINE METHYLSULFONIUM IODIDE is used as a research tool to study the role of methylation in biological processes, providing insights into the mechanisms of gene regulation and enzyme function.
Used in Pharmaceutical Industry:
L-METHIONINE METHYLSULFONIUM IODIDE is used as a precursor in the preparation of methylated nucleotides, which are essential components of various pharmaceuticals, contributing to their therapeutic effects.
Used in Agrochemical Industry:
L-METHIONINE METHYLSULFONIUM IODIDE is used in the synthesis of agrochemicals, including pesticides and herbicides, where its methyl donor properties are utilized to enhance the activity and selectivity of these compounds.
Used in Neurodegenerative Disease Treatment:
L-METHIONINE METHYLSULFONIUM IODIDE is being investigated for its potential use in the treatment of neurodegenerative diseases, leveraging its anti-inflammatory and antioxidant properties to protect neurons and slow disease progression.
Used in Cancer Therapy:
L-METHIONINE METHYLSULFONIUM IODIDE has been explored for its potential role in cancer treatment, with its methyl donor capabilities and anti-inflammatory properties being studied for their impact on tumor growth and metastasis.

InChI:InChI=1/C5H11NO2S.CH4S.HI/c1-9-3-2-4(6)5(7)8;1-2;/h4H,2-3,6H2,1H3,(H,7,8);2H,1H3;1H/t4-;;/m0../s1

Upstream product

• 63-68-3 L-methionine 
• 74-88-4 methyl iodide 
• 62965-24-6 (S-tert-butyl)-homocysteine 
• 59-51-8 (+)-methionine 

Downstream Products

• 672-15-1 L-homoserine 
• 1927-25-9 DL-Homoserine 
• 3211-76-5 Seleno-L-methionine 
• 127628-31-3 (l)α-amino-γ-butyrolactone hydroiodide 

Relevant academic research and scientific papers

Method for preparing L-selenomethionine

The invention discloses a method for preparing L-selenomethionine and belongs to the field of additives. The method comprises the following steps: A. subjecting L-methionine and iodomethane to a reaction in water, so as to obtain an intermediate; and B. subjecting the intermediate and selenium sodium methoxide to a reaction in an alcoholic solvent, carrying out quenching with glacial acetic acid after the reaction ends up, adjusting a pH value of a reaction system to 5 to 6, and carrying out filtering and baking, thereby obtaining the L-selenomethionine. The method has the beneficial technicaleffects that the intermediate is simpler in preparation and lower in cost; the preparation operation of the intermediate is simpler; and employed raw materials and reagents are commercially available, a reaction process is free of production of fetid and hypertoxic byproduct, and thus, the method is more beneficial to labor protection and environments.

Rhodium(I) and Iridium(I) N-Heterocyclic carbene complexes of imidazolium functionalized amino acids and peptides

The conjugation of organometallic complexes to peptides is generally achieved through covalent organic linkages of the metal's ligand to the peptide. Examples of direct coordination to metal centers by amino acid side chain residues remain rare. In one such example, side chain methylation of the natural amino acid histidine (His) resulted in an imidazolium functionalized amino acid which was used for the synthesis of rhodium(I), iridium(I), iridium(III), palladium(II) and ruthenium(III) N-heterocyclic carbene (NHC) complexes of the single amino acid and peptides containing this amino acid. Here, we have synthesized two new, non-natural imidazolium functionalized amino acid derivatives, which were used for solid phase peptide synthesis and for the synthesis of [M(COD)(NHC)Cl] (COD = 1,5 cyclooctadiene) complexes of Rh(I) and Ir(I). In total, six new complexes of the single amino acids and four complexes where the amino acids are present in a peptide environment were synthesized. Their characterization provides convincing evidence of conversion of the imidazolium moiety to an NHC ligand and thus the presence of a direct metal-carbon bond between the metal center and the amino acid side chain. Therefore, our compounds represent unique examples of peptide-conjugated complexes that bear the potential to be used for the synthesis of N-heterocyclic carbene complexes conjugated to cancer cell targeting peptides.

Design, synthesis, and evaluation of compounds capable of reducing Pseudomonas aeruginosa virulence

Anti-virulence approaches in the treatment of Pseudomonas aeruginosa (PA)-induced infections have shown clinical potential in multiple in vitro and in vivo studies. However, development of these compounds is limited by several factors, including the lack of molecules capable of penetrating the membrane of gram-negative organisms. Here, we report the identification of novel structurally diverse compounds that inhibit PqsR and LasR-based signaling and diminish virulence factor production and biofilm growth in two clinically relevant strains of P. aeruginosa. It is the first report where potential anti-virulent agents were evaluated for inhibition of several virulence factors of PA. Finally, co-treatment with these inhibitors significantly reduced the production of virulence factors induced by the presence of sub-inhibitory levels of ciprofloxacin. Further, we have analyzed the drug-likeness profile of designed compounds using quantitative estimates of drug-likeness (QED) and confirmed their potential as hit molecules for further development.

Synthesis and biological evaluation of novel L-homoserine lactone analogs as quorum sensing inhibitors of pseudomonas aeruginosa

In this study, we synthesized four series of novel L-homoserine lactone analogs and evaluated their in vitro quorum sensing (QS) inhibitory activity against two biomonitor strains, Chromobacterium violaceum CV026 and Pseudomonas aeruginosa PAO1. Studies of the structure–activity relationships of the set of L-homoserine lactone analogs indicated that phenylurea-containing N-dithiocarbamated homoserine lactones are more potent than (Z)-4-bromo-5-(bromomethylene)-2(5H)-furanone (C30), a positive control for biofilm formation. In particular, compared with C30, QS inhibitor 11f significantly reduced the production of virulence factors (pyocyanin, elastase and rhamnolipid), swarming motility, the formation of biofilm and the mRNA level of QS-related genes regulated by the QS system of PAO1. These results reveal 11f as a potential lead compound for developing novel antibacterial quorum sensing inhibitors.

Reaction of (S)-homoserine lactone with Grignard reagents: synthesis of amino-keto-alcohols and β-amino acid derivatives

The ring-opening reaction of homoserine lactone with phenylmagnesium bromides was systematically examined. A reliable method to achieve β-amino acid precursors was developed by tuning the reaction conditions to favor mono-addition to the carbonyl moiety of the lactone.

Synthesis of Chiral Bicyclic Guanidinium Salts using Di(imidazole-1-yl)methanimine

A detailed account of the synthesis of chiral bicyclic guanidinium salts is presented. This work represents the first systematic investigation of an approach toward the challenging target molecules via a key guanylation step employing di(imidazole-1-yl)methanimine (6) followed by a two-fold cyclization, which resulted in guanidinium salts 8 and 10. Factors governing the regioselectivity of the final cyclization step are discussed based on further data obtained in the course of the attempted syntheses of two additional bicyclic guanidinium salts.

A homoserine lactone compounds, its preparation process and its application

The invention discloses homoserine lactone compounds as well as preparation methods and application thereof, relates to two series of compounds, i.e., N-acyl homoserine lactone and N-acetyl homoserine lactone, as well as preparation methods thereof, belonging to the chemical field of medicines, and in particular relates to a type of novel homoserine lactone compounds as shown in a chemical general formula described in the specification. According to the invention, mother nucleus of homoserine lactone is modified and an acyl side chain and a chalcone compound having large conjugated groups are introduced, thus improve quorum sensing inhibiting activity of the compound. The route preparation method is simple and easy to implement, and yield is high and reaches more than 70%.

Concise Synthesis of Enantiomerically Pure (1′S,2′R)-and (1′R,2′S)-2S-Amino-3-(2′-aminomethyl-cyclopropyl)propionic Acid: Two E-Diastereoisomers of 4,5-Methano-l-lysine

A concise synthesis of both E-isomers of 2S-amino-3-(2′-aminomethyl- cyclopropyl)propionic acid, new methano-l-lysines, is described. The synthetic route includes nine steps from l-methionine, with a key step involving the cyclopropanation of an intermediate E-allylic alcohol. The resultant hydroxymethylcyclopropanes were readily separated and converted into the title α-amino acids. The stereochemistry around the cyclopropane rings was deduced by conducting the cyclopropanation in the presence of N,N,N′,N′-tetramethyl-d-tartaric acid diamide butylboronate, a chiral controller which is known to favour the production of S-hydroxymethyl cyclopropanes from allylic alcohols.

PROCESSES FOR PREPARING AMINO-SUBSTITUTED GAMMA-LACTAMS

The present application describes general process for the preparation of amino-substitued gamma-lactams involving the reaction of synthons of the general Formulae (I) and (VI): with amines. The processes are amenable to solid phase synthetic techniques and therefore allow the efficient incorporation of amino-substitued gamma-lactams into a wide variety of structural scaffolds, including, in particular peptides.

Positional scanning for peptide secondary structure by systematic solid-phase synthesis of amino lactam peptides

Incorporation of amino lactams into biologically active peptides has been commonly used to restrict conformational mobility, enhance selectivity, and increase potency. A solid-phase method using a Fmoc-protection strategy has been developed for the systematic synthesis of peptides containing configurationally defined α- and β-amino γ-lactams. N-Alkylation of N-silyl peptides with five- and six-member cyclic sulfamidates 9 and 8 minimized bis-alkylation and provided N-alkyl peptides,which underwent lactam annulation under microwave heating. Employing th is solid-phase protocol on the growth hormone secretagogue GHRP-6, as well as on the allosteric modulator of the IL-1 receptor 101.10, has furnished 16 lactam derivatives and validated the effectiveness of this approach on peptides bearing aliphatic, aromatic, branched, charged, and heteroatomic side chains. The binding affinity IC 50 values of the GHRP-6 lactam analogues on both the GHS-R1a and CD36 receptors are reported as well as inhibition of thymocyte proliferation measurements for the 101.10 lactam analogues. In these cases, lactam analogues were prepared exhibiting similar or improved properties compared with the parent peptide. Considering the potential for amino lactams to induce peptide turn conformations, the effective method described herein for their supported construction on growing peptides, and for the systematical amino lactam scan of peptides, has proven useful for the rapid identification of the secondary structure necessary for peptide biological activity.