Cyclo(Ile-Leu) is a hydrophobic diketopiperazine featuring constrained backbone geometry and high stability. Researchers examine its stereochemical effects on packing, solubility, and hydrogen-bonding limitations. The scaffold models minimal cyclic hydrophobic motifs. Applications include peptidomimetic development, DKP-based material design, and conformational studies.
CAT No: R2598
CAS No:91741-17-2
Synonyms/Alias:Cyclo(Ile-Leu);Cyclo-(Leu-Ile);91741-17-2;CHEBI:203084;AKOS012403841;FS-6957;3-(sec-Butyl)-6-isobutylpiperazine-2,5-dione;3-butan-2-yl-6-(2-methylpropyl)piperazine-2,5-dione;3-(2-methylpropyl)-6-(sec-butyl)piperazine-2,5-dione;
Cyclo(Ile-Leu), also known as cyclo(L-isoleucyl-L-leucyl), is a cyclic dipeptide formed by the head-to-tail cyclization of the amino acids isoleucine and leucine. As a member of the diketopiperazine (DKP) family, it is recognized for its structural rigidity and distinctive physicochemical properties, which make it a valuable probe in peptide chemistry and natural product research. Its occurrence in various microbial and plant systems has drawn attention to its potential roles in intercellular communication, signaling, and secondary metabolism. The conformational stability and resistance to enzymatic degradation characteristic of cyclic dipeptides like cyclo(Ile-Leu) have positioned it as a useful model compound for studying peptide cyclization, bioactivity, and structure-function relationships in biochemical investigations.
Peptide chemistry research: Cyclo(Ile-Leu) serves as a model compound in the study of peptide cyclization mechanisms and diketopiperazine formation. Its well-defined cyclic structure allows researchers to investigate the thermodynamics and kinetics of ring closure reactions, providing insights into the factors governing cyclization efficiency and selectivity. Such studies are instrumental in optimizing synthetic strategies for cyclic peptides, which are of growing interest due to their enhanced stability and diverse biological activities.
Natural product biosynthesis studies: The compound is frequently utilized as a reference standard or analytical marker in the exploration of microbial and plant-derived natural products. Its presence in fermentation broths or plant extracts can indicate specific biosynthetic pathways, such as nonribosomal peptide synthesis or spontaneous cyclization events. By tracking the formation and distribution of cyclo(Ile-Leu), scientists can elucidate metabolic routes, regulatory mechanisms, and ecological functions associated with cyclic dipeptides in various organisms.
Structure-activity relationship (SAR) analysis: The conformational constraints imposed by the diketopiperazine ring system make cyclo(Ile-Leu) an excellent scaffold for SAR studies. By comparing its physicochemical and biological properties with those of related cyclic and linear dipeptides, researchers can probe the influence of ring size, side-chain composition, and stereochemistry on molecular recognition, binding affinity, and bioactivity. These insights are valuable for the rational design of peptide-based ligands, inhibitors, or molecular probes.
Analytical method development: As a chemically stable and structurally defined analyte, cyclo(Ile-Leu) is employed in the development and validation of chromatographic and spectroscopic techniques for peptide analysis. Its use as a calibration standard or test compound assists in optimizing separation parameters, detection sensitivity, and quantification accuracy in high-performance liquid chromatography (HPLC), mass spectrometry, and nuclear magnetic resonance (NMR) applications. Such methodological advancements facilitate the reliable characterization of cyclic peptides in complex biological samples.
Peptide-based material science: The inherent stability and self-assembling potential of diketopiperazines have prompted interest in their application to material science and nanotechnology. Cyclo(Ile-Leu), with its hydrophobic side chains and cyclic backbone, can contribute to studies on peptide-driven supramolecular assembly, gel formation, or nanostructure fabrication. These investigations may inform the design of novel biomaterials, drug delivery vehicles, or functional coatings leveraging the unique properties of cyclic dipeptides.
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