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| Description | Cyclo(L-Pro-L-Val) (CAS: 2854-40-2, cyclo(-Pro-Val)) is the minimal 2,5-diketopiperazine cyclic dipeptide formed by head-to-tail amide cyclization of L-proline and L-valine, molecular formula C10H16N2O2, MW 196.25 Da. This DKP scaffold is widely produced by bacteria, fungi, and plants, showing antifungal activity and inhibition of Gram-positive phytopathogenic bacteria, and is regarded as a biopesticide lead; DKPs also act as inter-kingdom quorum-sensing signals in bacterial-fungal communication. Cyclo(L-Pro-L-Val) is a tool for diketopiperazine conformation, cyclic-dipeptide bioactivity, and natural-product small molecules. |
| Structure type | Cyclic dipeptide (2,5-diketopiperazine, cyclo(L-Pro-L-Val)) |
| Solubility | Readily soluble in methanol, DMSO; sparingly soluble in water |
| Storage | Powder -20C, dry, protected from light |
Product Basic Information Table
| Product Standard English Name | Product Abbreviation / Alias | Function Tags (comma-separated) | Core Structure | Molecular Formula | Exact Mass (Da) | Average MW (Da) | Salt Form | Length (aa) |
| Cyclo(L-Pro-L-Val) (cyclic dipeptide / 2,5-diketopiperazine) | Cyclo(L-Pro-L-Val); cyclo(-Pro-Val); cyclo(L-prolyl-L-valyl); cyclic dipeptide; 2,5-diketopiperazine; DKP; 3,6-disubstituted piperazine-2,5-dione; CAS 2854-40-2; Cyclo-Val-Pro DKP | cyclic dipeptide, 2,5-diketopiperazine (DKP), small-molecule natural product, neutral lipophilic, no free termini, antifungal/antibacterial, neuroactive, microbial secondary metabolite, non-linear peptide | Non-linear small-molecule cyclic dipeptide formed by cyclization of L-prolyl-L-valine through two amide bonds into a 2,5-diketopiperazine (DKP), i.e., a 3,6-disubstituted piperazine-2,5-dione; SMILES: CC(C)C1C(=O)N2CCCC2C(=O)N1; the Pro pyrrolidine ring is fused to the DKP six-membered ring, and Val bears an isopropyl side chain; no free N-terminal amine and no free C-terminal carboxyl (both termini are locked in the cyclic diamide), overall neutral; the two amide N and two carbonyl O form a polar core, while the Pro pyrrolidine and Val isopropyl confer lipophilicity; not an amphipathic alpha-helix but a rigid planar six-membered DKP scaffold | C10H16N2O2 | 196.121 | 196.25 | Neutral free molecule (no salt); CAS 2854-40-2, formula C10H16N2O2, exact mass 196.121 Da / avg MW 196.25 Da (NIST/MuseChem/BOC Sciences agree) | 2 |
Physicochemical Solubility & Storage Parameters
| Product Code | Appearance | Long-term Storage | Short-term Storage | Solution Stability | Solid Powder Stability |
| PEP-CPLV-01 | White to off-white crystalline powder | Room temperature or 2-8°C, desiccated and sealed; DKP ring is stable, no oxidation/reduction/photo-sensitive residues; no Met/Cys/Trp; routine sealed storage with moisture protection | Room temperature, desiccated, stable | Small DKP molecule, moderate-to-low aqueous solubility, relatively lipophilic; soluble in methanol, ethanol, DMSO; prepare stock solutions in DMSO or ethanol (10-50 mg/mL) and dilute into assay buffers; no net charge, pH-independent solubility | Crystalline solid is stable; the DKP ring is chemically robust and protease-resistant (cyclic structure evades exopeptidases); long-term storage at room temperature, sealed and dry |
Functional Description
| Product Code | Frontend Short Summary | Detailed Biological Function Description | Applicable Research Areas (comma-separated) | Targets / Pathways |
| PEP-CPLV-01 | A 2,5-diketopiperazine (DKP) cyclic dipeptide formed by cyclization of L-proline and L-valine (C10H16N2O2, MW 196.25), neutral with no free termini, lipophilic, with antifungal/antibacterial and neuroactive properties; a tool compound for DKP natural-product research. | Cyclo(L-Pro-L-Val) is a 2,5-diketopiperazine (DKP) cyclic dipeptide formed by double amide condensation between L-proline and L-valine, structurally a 3,6-disubstituted piperazine-2,5-dione in which the Pro pyrrolidine ring is fused to the DKP six-membered ring and Val carries an isopropyl side chain. DKP is the most common cyclic dipeptide scaffold in nature, widely found in bacteria (including Mycobacterium), fungi, marine organisms, and fermented foods (bread, wine, soy sauce). Unlike linear peptides, the two amino acid termini of a DKP are locked in the cyclic diamide-there is no free N-terminal amine or C-terminal carboxyl-the molecule is overall neutral, and it adopts a rigid planar conformation with high metabolic stability: the cyclic structure evades recognition by conventional exopeptidases. Cyclo(L-Pro-L-Val) displays diverse bioactivities: it is antibacterial against plant-pathogenic microorganisms (e.g., Rhodococcus fascians), inhibits fungal growth, and some DKP congeners show neuroactive and anti-inflammatory activity and function as quorum-sensing signal mimics regulating bacterial behavior. In food science, Pro-Val DKP is a common flavor/bioactive component of wheat sourdough and fermented foods and acts synergistically with lactic acid. This product is a small molecule (MW only 196.25 Da), not a conventional 21+ amino acid AMP; it serves as a DKP-class natural-product research tool for microbial secondary metabolism, food fermentation chemistry, quorum sensing, and central neuroactivity studies. | 2,5-diketopiperazine (DKP) natural products, cyclic dipeptide chemistry, microbial secondary metabolism, antifungal/antibacterial small molecules, food fermentation chemistry, quorum-sensing signals, neuroactive compounds, protease-stable cyclic scaffolds | microbial cell membrane/wall targets, fungal growth inhibition, plant pathogens (R. fascians), quorum-sensing signaling pathways, CNS receptors (in select DKP congeners) |
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