L-Methionyl-L-methionine integrates two sulfur-containing residues that offer insight into oxidation reactions and redox-sensitive folding. The dipeptide supports studies of methionine-dependent conformational changes. Researchers explore its behavior in solvent environments and enzymatic assays. Uses include metabolic modeling, peptide synthesis refinement, and reactive-site analysis.
CAT No: R2653
CAS No:7349-78-2
Synonyms/Alias:H-MET-MET-OH;7349-78-2;L-Methionyl-L-methionine;Met-Met;L-Methionine, L-methionyl-;CHEMBL1222165;CHEBI:74707;Methionyl-Methionine;(2S)-2-[[(2S)-2-amino-4-methylsulfanylbutanoyl]amino]-4-methylsulfanylbutanoic acid;(S)-2-((S)-2-Amino-4-(methylthio)butanamido)-4-(methylthio)butanoic acid;L-Met-L-Met;H-L-Met-L-Met-OH;MFCD00038230;N-methionyl-methionine;SCHEMBL1157691;ZYTPOUNUXRBYGW-YUMQZZPRSA-N;BDBM50350482;AKOS010408816;FM108130;MS-23985;HY-150013;CS-0534907;NS00058698;Q27144845;
L-Methionyl-L-methionine is a synthetic dipeptide composed of two L-methionine residues linked by a peptide bond. As a member of the peptide compound family, it is of considerable interest in biochemical research due to its relevance to sulfur-containing amino acid metabolism, peptide transport, and protein engineering. The presence of methionine at both termini imparts unique chemical and structural properties, making it a valuable tool for probing peptide stability, enzymatic specificity, and methionine-related biochemical pathways. Its defined structure and high degree of purity enable precise experimental manipulation, supporting a range of investigations in the fields of biochemistry, molecular biology, and peptide science.
Peptide transport studies: L-Methionyl-L-methionine serves as a model substrate for investigating the mechanisms of peptide transporter systems, such as those in bacterial and mammalian cells. Researchers utilize this dipeptide to assess the specificity, affinity, and kinetics of peptide uptake across cellular membranes, providing insights into nutrient absorption and peptide-based drug delivery. Its structural simplicity and defined composition facilitate controlled experiments that elucidate the molecular determinants of transporter recognition and translocation.
Enzymatic hydrolysis research: The compound is frequently employed in studies of peptidase and protease activity, particularly those enzymes with specificity for methionine-containing peptides. By serving as a substrate in enzymatic assays, it enables the characterization of cleavage patterns, substrate preferences, and catalytic efficiencies. Such investigations are instrumental in mapping the substrate scope of aminopeptidases, endopeptidases, and other proteolytic enzymes, contributing to a deeper understanding of protein turnover and peptide metabolism.
Peptide synthesis optimization: In the context of synthetic peptide chemistry, L-Methionyl-L-methionine is utilized as a reference compound or building block to evaluate coupling strategies, protecting group compatibilities, and purification protocols. Its well-defined structure makes it an ideal standard for calibrating chromatographic systems and verifying synthetic yields. Moreover, its use can inform the development of more efficient methodologies for assembling methionine-rich peptides, which are often challenging due to the reactivity of the sulfur-containing side chain.
Protein engineering and structural studies: The dipeptide is valuable in research focused on protein engineering, folding, and stability. It can be incorporated into model systems to assess the impact of methionine residues on peptide conformational dynamics, aggregation tendencies, and oxidative susceptibility. Such studies enhance the understanding of methionine's role in protein structure-function relationships and inform the design of peptides and proteins with tailored properties for industrial or research applications.
Analytical method development: L-Methionyl-L-methionine is also employed as a calibration standard or test analyte in the development and validation of analytical techniques, including high-performance liquid chromatography (HPLC) and mass spectrometry. Its consistent physicochemical properties make it suitable for optimizing detection sensitivity, retention behavior, and quantification accuracy in peptide analysis workflows. The availability of this dipeptide supports laboratories in establishing robust, reproducible methods for the qualitative and quantitative assessment of peptide samples.
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