3493-11-6

Basic information

• Product Name: L-METHIONINE METHYLSULFONIUM IODIDE
• Synonyms: L-METHIONINE METHYLSULFONIUM IODIDE;L-methionine-S-methylsulfonium iodine;L-methionine-s-methylsulfoniumiodidecrystalline;Methionine-S-methylsulfonium iodide crystalline;[(3S)-3-amino-4-hydroxy-4-keto-butyl]-dimethyl-sulfonium iodide;[(3S)-3-amino-4-hydroxy-4-oxobutyl]-dimethylsulfanium iodide;[(3S)-3-azanyl-4-hydroxy-4-oxo-butyl]-dimethyl-sulfanium iodide;(3-AMINO-3-CARBOXYPROPYL)DIMETHYLSULFONIUM IODIDE
• CAS NO: 3493-11-6
• Molecular Formula: C₆H₁₄NO₂S*I
• Molecular Weight: 291.15
• EINECS: 251-893-0
• Mol File: 3493-11-6.mol
• Article Data: 18

Chemical Properties

• Melting Point: 150 °C (decomp)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: L-METHIONINE METHYLSULFONIUM IODIDE(CAS DataBase Reference)
• NIST Chemistry Reference: L-METHIONINE METHYLSULFONIUM IODIDE(3493-11-6)
• EPA Substance Registry System: L-METHIONINE METHYLSULFONIUM IODIDE(3493-11-6)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 3493-11-6(Hazardous Substances Data)

Usage

General Description

L-Methionine Methylsulfonium Iodide, also known as MMi, is a chemical compound derived from the amino acid L-methionine. It is a methylated derivative of L-methionine and is commonly used in organic synthesis and as a reagent in biochemical research. MMi is known for its ability to serve as a methyl donor in various biological processes, and it also has anti-inflammatory and antioxidant properties. The compound is often used in the preparation of methylated nucleotides, as well as in the synthesis of various pharmaceuticals and agrochemicals. Additionally, MMi has been investigated for its potential use in the treatment of neurodegenerative diseases and cancer.

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 
• 59-51-8 (+)-methionine 
• 62965-24-6 (S-tert-butyl)-homocysteine 

Downstream Products

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

Relevant articles and documents

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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.

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.