Pro-Ile forms a dipeptide with conformational restriction from proline and hydrophobic packing from isoleucine. The sequence provides a model for β-turn initiation and sterically constrained folding. Researchers study solvent effects and backbone geometry. Uses include structural modeling, peptide synthesis research, and conformational analysis.
CAT No: R2662
CAS No:51926-51-3
Synonyms/Alias:H-Pro-Ile-OH;51926-51-3;Prolylisoleucine;Pro-ile;l-prolyl-l-isoleucine;L-Pro-L-Ile;CHEBI:74790;(2S,3S)-3-Methyl-2-((S)-pyrrolidine-2-carboxamido)pentanoic acid;N-L-Prolyl-L-isoleucine;(2S,3S)-3-methyl-2-[[(2S)-pyrrolidine-2-carbonyl]amino]pentanoic acid;DTXSID20874265;Prolyl-isoleucine;l-prolylisoleucine;H-Pro-Ile;MFCD00037868;CHEMBL55967;SCHEMBL8720606;OCYROESYHWUPBP-CIUDSAMLSA-N;DTXCID601012395;AKOS010420273;FP108157;HY-124005;CS-0083849;Q27144901;(2S,3S)-3-methyl-2-{[(2S)-pyrrolidin-2-yl]formamido}pentanoic acid;
Pro-Ile, also known as Prolyl-Isoleucine, is a dipeptide composed of the amino acids proline and isoleucine linked by a peptide bond. As a member of the dipeptide class, it exhibits unique physicochemical properties that distinguish it from individual amino acids and longer peptides. Its structural simplicity, combined with the functional groups contributed by proline and isoleucine, makes it a valuable tool in biochemical research, peptide structure-function studies, and analytical method development. The compound's relevance extends to investigations of peptide stability, enzymatic processing, and transport phenomena, providing researchers with a model system for exploring fundamental aspects of peptide chemistry and biology.
Peptide structure-activity relationship studies: Prolyl-Isoleucine serves as a model dipeptide for probing the relationship between peptide sequence and biological activity. Its defined structure enables systematic analysis of how proline's cyclic imino group and isoleucine's hydrophobic side chain influence peptide conformation, stability, and interactions with proteins or enzymes. Researchers often employ this dipeptide in comparative studies to elucidate the impact of specific residue combinations on recognition by proteases, peptide transporters, or binding partners, thereby contributing to a deeper understanding of peptide-mediated signaling and recognition mechanisms.
Analytical method development: In the context of chromatography and mass spectrometry, Pro-Ile is frequently utilized as a standard or reference compound for optimizing detection and quantification protocols. Its well-characterized mass and retention properties make it suitable for calibrating analytical instruments, validating separation methods, and assessing the performance of peptide analysis workflows. The use of this dipeptide as an internal or external standard supports accurate quantification and reproducibility in peptide profiling experiments, particularly in complex biological matrices.
Enzymatic specificity and kinetics research: The dipeptide's defined sequence is advantageous for studies investigating the substrate specificity and catalytic efficiency of peptidases and proteolytic enzymes. By monitoring the hydrolysis of Prolyl-Isoleucine under controlled conditions, researchers can characterize enzyme selectivity, determine kinetic parameters, and evaluate the influence of sequence context on enzymatic processing. Such investigations are critical for understanding the mechanisms governing peptide turnover, degradation pathways, and the design of enzyme inhibitors or substrates.
Peptide transporter and absorption studies: Pro-Ile is also employed in research focused on peptide uptake and transport mechanisms across biological membranes. Its small size and specific amino acid composition make it an informative probe for characterizing the activity of oligopeptide transporters in cellular or tissue models. Studies utilizing this dipeptide help delineate the substrate preferences, transport kinetics, and regulatory factors influencing peptide absorption, thereby advancing knowledge in nutrient uptake, drug delivery, and membrane biology.
Peptide synthesis optimization: In the field of synthetic peptide chemistry, Prolyl-Isoleucine is used as a model compound to evaluate and refine coupling strategies, protecting group schemes, and purification protocols. Its incorporation into synthetic workflows allows chemists to assess the efficiency of peptide bond formation, monitor side reactions, and troubleshoot synthetic challenges associated with proline-containing sequences. Insights gained from such studies facilitate the development of robust methodologies for the assembly of more complex peptides and peptide-based materials.
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