Cyclo(Pro-Trp) is a cyclic dipeptide molecule composed of the two amino acids proline and tryptophan. Cyclo(Pro-Trp) is found in some proteins that are involved in the regulation of cell growth and differentiation. It has also been found to possess potential anti-inflammatory and anti-cancer properties.
CAT No: 10-101-252
CAS No:67889-75-2
Synonyms/Alias:Cyclo(Pro-Trp);67889-75-2;3-(1H-indol-2-ylmethyl)-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione;
Cyclo(Pro-Trp), also known as cyclo(L-prolyl-L-tryptophyl), is a cyclic dipeptide composed of the amino acids proline and tryptophan. As a member of the diketopiperazine family, it features a stable six-membered ring structure formed through the cyclization of its constituent amino acids. This structural motif imparts unique physicochemical properties, including enhanced metabolic stability and resistance to enzymatic degradation, making it a valuable tool in various biochemical and molecular investigations. Widely recognized for its occurrence in natural sources such as microbial metabolites and food-derived peptides, Cyclo(Pro-Trp) is of significant interest to researchers studying peptide chemistry, bioactive compound discovery, and molecular interaction mechanisms.
Peptide Research: Cyclo(Pro-Trp) is frequently utilized in peptide research to explore the conformational preferences and structural dynamics of cyclic dipeptides. Its rigid, well-defined ring system serves as a model for studying intramolecular hydrogen bonding, aromatic stacking, and backbone torsion angles, which are critical factors in understanding peptide folding and stability. Investigators leverage its characteristic structure to gain insights into the relationship between peptide conformation and biological function, aiding in the rational design of novel peptide-based molecules.
Bioactive Compound Screening: The compound is extensively investigated in bioactive compound screening programs, particularly in the context of natural product chemistry and microbial metabolomics. As a naturally occurring diketopiperazine, it is often included in compound libraries to assess its potential modulatory effects on biological targets such as enzymes, receptors, or signaling pathways. Its presence in microbial secretomes and fermented foods further underscores its relevance in studies aiming to identify new bioactive peptides with potential applications in agriculture, food science, and biotechnology.
Peptide Synthesis Optimization: Cyclo(Pro-Trp) serves as a valuable reference standard and synthetic intermediate in the development and optimization of peptide synthesis methodologies. Researchers employ it to benchmark cyclization strategies, evaluate coupling reagents, and refine purification techniques for cyclic dipeptides. Its well-characterized properties make it an ideal candidate for validating synthetic protocols, ensuring reproducibility, and troubleshooting challenges encountered during the preparation of more complex cyclic peptides.
Analytical Method Development: The compound is instrumental in the development and validation of analytical techniques for peptide characterization. Its defined molecular structure and distinct chromatographic and spectroscopic signatures make it a preferred standard for calibrating high-performance liquid chromatography (HPLC), mass spectrometry, and nuclear magnetic resonance (NMR) platforms. Analytical chemists utilize it to optimize detection parameters, assess method sensitivity, and verify the accuracy of peptide quantification in complex biological matrices.
Molecular Interaction Studies: Cyclo(Pro-Trp) is also employed in molecular interaction studies aimed at elucidating the binding properties and interaction mechanisms of cyclic dipeptides with various biomolecules. Its aromatic and hydrophobic features enable researchers to probe non-covalent interactions such as π-π stacking, hydrophobic contacts, and hydrogen bonding with proteins, nucleic acids, or lipid membranes. These investigations provide valuable data on the molecular determinants of peptide recognition and binding specificity, contributing to the broader understanding of peptide-mediated biological processes.
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