Cyclo-(L-Pro-L-Ile) is a diketopiperazine ring formed by cyclization of proline and isoleucine, producing a rigid scaffold with constrained backbone geometry. The bicyclic core enhances stability and modulates hydrophobic interactions. Researchers use it to explore β-turn mimicry, ligand-protein contacts, and conformation-dependent dynamics. Its compact structure supports detailed mechanistic and biophysical studies.
CAT No: R2279
CAS No:57089-60-8
Synonyms/Alias:57089-60-8;Cyclo-(L-Pro-L-Ile);Cyclo(Ile-Pro);cyclo(isoleucyl-prolyl);CHEMBL499545;BDBM163708;Cyclo L-Pro-L-Ile (Fr. 1-5);ARD183733;AKOS040734722;FC165819;1ST183733;(3S,8aS)-3-((S)-sec-Butyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione;(3S,8aS)-3-[(2S)-butan-2-yl]-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione;(3S,8aS)-3-[(2S)-butan-2-yl]-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione;
Cyclo-(L-Pro-L-Ile) is a cyclic dipeptide composed of L-proline and L-isoleucine residues linked via a peptide bond in a diketopiperazine ring structure. As a member of the diketopiperazine family, this compound exhibits notable conformational rigidity and enhanced metabolic stability compared to linear peptides. Its unique cyclic architecture imparts distinct physicochemical properties, making it a valuable tool in peptide chemistry, molecular recognition studies, and investigations of peptide-based bioactivity. Researchers are increasingly interested in such cyclic dipeptides for their structural diversity and potential roles as scaffolds in synthetic and analytical applications.
Peptide synthesis research: Cyclo-(L-Pro-L-Ile) serves as a model system for studying the formation and stability of cyclic dipeptides, which are important intermediates and end-products in peptide synthesis. Investigators utilize this compound to examine cyclization reactions, peptide bond formation, and the influence of side-chain characteristics on ring closure efficiency. Insights gained from these studies inform the design of synthetic strategies for more complex cyclic peptides and peptide mimetics, supporting advancements in peptide engineering.
Structural biology and conformational analysis: The rigid, well-defined structure of this diketopiperazine makes it an excellent reference compound for conformational studies using spectroscopic and crystallographic techniques. It is frequently employed to calibrate analytical instruments or to benchmark computational models that predict peptide folding and ring strain. Such studies contribute to a deeper understanding of the relationship between peptide sequence, ring size, and three-dimensional conformation, which is critical for rational design in peptide science.
Molecular recognition and supramolecular chemistry: Due to its cyclic nature and the presence of both hydrophobic and polar residues, Cyclo-(L-Pro-L-Ile) is used in research focused on molecular recognition processes. Its ability to participate in hydrogen bonding, π-π stacking, and hydrophobic interactions makes it a useful probe for studying host-guest chemistry, peptide-receptor interactions, and the assembly of supramolecular structures. These investigations aid in elucidating the principles underlying selective binding and molecular self-organization.
Analytical method development: The compound is employed as a standard or reference material in the development and validation of chromatographic and mass spectrometric techniques for peptide analysis. Its defined mass, stability, and retention characteristics enable researchers to optimize detection parameters, assess method sensitivity, and evaluate instrument performance. Such applications are essential for ensuring the reliability of peptide quantification and characterization workflows in both academic and industrial laboratories.
Biochemical pathway studies: Cyclo-(L-Pro-L-Ile) is also utilized in research exploring the biosynthesis and metabolic fate of diketopiperazines in microbial and plant systems. By tracing its formation and degradation, scientists can investigate the enzymatic mechanisms responsible for cyclic peptide production and turnover. These studies provide valuable information about natural product biosynthesis, metabolic regulation, and the ecological roles of cyclic dipeptides in various biological contexts.
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