Chemical Property of cyclo(L-Pro-L-Val)
Chemical Property:
- Melting Point:190-192 °C
- Boiling Point:420.7±34.0 °C(Predicted)
- PKA:13.15±0.40(Predicted)
- PSA：49.41000
- Density:1.17±0.1 g/cm3(Predicted)
- LogP:0.39850
- Storage Temp.:-15°C
- Solubility.:Chloroform (Slightly, Sonicated), Methanol (Slightly)
- XLogP3:0.8
- Hydrogen Bond Donor Count:1
- Hydrogen Bond Acceptor Count:2
- Rotatable Bond Count:1
- Exact Mass:196.121177757
- Heavy Atom Count:14
- Complexity:275
- Purity/Quality:
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99% *data from raw suppliers
Cyclo(L-prolyl-L-valyl) *data from reagent suppliers
Safty Information:
- Pictogram(s):
- Hazard Codes:
- MSDS Files:
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SDS file from LookChem
Useful:
- Canonical SMILES:CC(C)C1C(=O)N2CCCC2C(=O)N1
- Isomeric SMILES:CC(C)[C@H]1C(=O)N2CCC[C@H]2C(=O)N1
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Description
Cyclo(L-Pro-L-Val) is a diketopiperazine that has been found in the marine sponge T. ignis, the bacterium B. pumilus, and the fungus A. fumigatus, among others. It is active against the bacteria S. aureus and B. subtilis (MICs = 16.3 and 18.2 μg/ml, respectively) but not E. coli (MIC = >20 μg/ml). Cyclo(L-Pro-L-Val) inhibits activation of a LuxR-dependent E. coli biosensor by the quorum-sensing molecule 3-oxo-hexanoyl-homoserine lactone (IC50 = 0.4 mM) and activates violacein pigment production in the LuxR-dependent C. violaceum acyl homoserine lactone reporter strain CV026. However, it does not activate or inhibit lacZ-based reporter fusions in S. liquefaciens or A. tumefaciens.
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Uses
Cyclo(L-Pro-L-Val) is a diketopiperazine formed by the fusion of valine and proline, reported as a secondary metabolite of fungi and bacteria. In Pseudomonas aeruginosa, cyclo(L-Pro-L-Val) is capable of activating N-acylhomoserine lactones (AHLs). Cyclo(L-Pro-L-Val) is also capable of activating or antagonizing other LuxR-based quorum-sensing systems. While the mode of action of the cyclo(L-Pro-L-Val) is not known, its activity suggests the existence of cross talk among bacterial signalling systems. Cyclo(L-prolyl-L-valyl) is a metabolite found in various marine fungi and bacteria. It is a diketopiperazine derivative isolated from Bacillus thuringiensis and Bacillus endophyticus.
