Cyclo(-Met-Pro) forms a diketopiperazine ring linking methionine and proline in a compact, conformationally restricted scaffold. The thioether side chain offers a handle for redox chemistry and metal-binding studies. Researchers investigate its backbone geometry, hydrogen bonding, and pH-dependent behavior. Applications include cyclic-dipeptide modeling, natural-product mimicry, and stability profiling.
CAT No: R2571
CAS No:53049-06-2
Synonyms/Alias:Cyclo(-Met-Pro);cyclo(methionylpropyl);53049-06-2;(3S,8aS)-3-(2-methylsulfanylethyl)-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione;MFCD03093468;CHEMBL463747;SCHEMBL16853544;DTXSID601346730;HMS1702I07;HY-P1937;STL565779;AKOS000739486;FC108324;CS-0100109;BRD-K00331588-001-01-2;(3S,8AS)-3-(2-(methylthio)ethyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione;(3S,8aS)-3-[2-(methylsulfanyl)ethyl]hexahydropyrrolo[1,2-a]pyrazine-1,4-dione;
Cyclo(-Met-Pro), also known as cyclo(methionyl-prolyl) or methionylproline cyclic dipeptide, is a diketopiperazine (DKP) compound formed by the cyclization of methionine and proline amino acids. As a member of the cyclic dipeptide family, it exhibits unique conformational rigidity and stability, making it a valuable scaffold in biochemical and pharmaceutical research. Its structure confers resistance to enzymatic degradation, allowing it to persist under various experimental conditions. Researchers are increasingly interested in cyclo(-Met-Pro) due to its presence in natural products and its potential roles in modulating biological processes. Its compatibility with both aqueous and organic systems further enhances its versatility for a wide range of scientific applications.
Peptide Engineering: In peptide engineering, cyclo(-Met-Pro) serves as a model scaffold for the synthesis of novel peptide-based molecules. Its cyclic structure imparts conformational constraints that are highly desirable for studying the relationship between peptide shape and biological activity. Scientists utilize this cyclic dipeptide to design analogs with enhanced stability, bioavailability, and receptor selectivity. The incorporation of methionine and proline residues also allows for the exploration of sulfur-containing side chains and proline-induced kinks, which are crucial for mimicking bioactive peptide motifs.
Chemical Biology Probes: As a chemical biology tool, methionylproline DKP is employed in the development of small molecule probes to investigate protein-protein interactions and cellular signaling pathways. Its stable, compact ring system can be functionalized to introduce fluorescent tags or affinity handles, facilitating the visualization and isolation of target proteins in complex biological samples. Such modifications enable researchers to dissect molecular mechanisms and identify novel interaction partners, advancing the understanding of cellular networks.
Natural Product Research: Within natural product chemistry, cyclo(-Met-Pro) is studied as a component of microbial secondary metabolites and food-derived peptides. Its occurrence in fermented products and microbial cultures has prompted investigations into its biosynthetic origins, ecological functions, and potential bioactivities. Researchers analyze its presence using advanced chromatographic and spectrometric techniques, seeking to elucidate its role in microbial communication or as a precursor in the biosynthesis of more complex natural products.
Material Science: In materials research, cyclo(methionyl-prolyl) is explored for its self-assembly properties and potential as a building block for nanostructured materials. The rigid, cyclic backbone promotes specific molecular interactions that can drive the formation of supramolecular architectures, such as nanotubes or hydrogels. These assemblies are of particular interest for developing biomimetic materials, drug delivery systems, and responsive surfaces, where the peptide's structural features enable precise control over material properties.
Enzyme Substrate Studies: Cyclo(-Met-Pro) is also utilized in enzymology as a substrate or inhibitor for peptidases and diketopiperazine-processing enzymes. Its resistance to nonspecific proteolysis makes it an excellent candidate for probing the specificity and catalytic mechanisms of enzymes involved in cyclic peptide metabolism. By monitoring its transformation or stability in enzymatic assays, scientists gain insights into enzyme function, substrate recognition, and potential routes for enzyme inhibition, which is valuable for both fundamental research and the development of novel enzyme modulators.
Analytical Method Development: In analytical chemistry, cyclo(-Met-Pro) is employed as a reference standard or calibration compound for chromatographic and mass spectrometric methods. Its well-defined structure and stability under analytical conditions make it suitable for method validation, quantification, and the assessment of instrument performance. Researchers leverage its properties to optimize separation protocols, ensure reproducibility, and facilitate the identification of related cyclic dipeptides in complex matrices, thereby supporting the advancement of analytical techniques in peptide research.
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