ChemicalBook > CAS DataBase List > CYCLO(-PRO-VAL)

CYCLO(-PRO-VAL)

Product Name
CYCLO(-PRO-VAL)
CAS No.
2854-40-2
Chemical Name
CYCLO(-PRO-VAL)
Synonyms
c(Pro-Val);Cyclo(Val-Pro);CYCLO(-PRO-VAL);Cyclo(L-Val-L-Pro-);Cyclo(L-Pro-L-Val-);2854-40-2/5654-87-5;Cyclo(L-prolyl-L-valyl);CYCLO(L-PROLYL-L-VALINE);Vildagliptin Impurity 114;Cyclo(L-Pro-L-Val),CYCLO(-PRO-VAL)
CBNumber
CB0132749
Molecular Formula
C10H16N2O2
Formula Weight
196.25
MOL File
2854-40-2.mol
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CYCLO(-PRO-VAL) Property

Melting point:
190-192 °C
Boiling point:
420.7±34.0 °C(Predicted)
Density 
1.17±0.1 g/cm3(Predicted)
storage temp. 
Sealed in dry,Room Temperature
solubility 
Chloroform (Slightly, Sonicated), Methanol (Slightly)
form 
Solid
pka
13.15±0.40(Predicted)
color 
White to Off-White
Sequence
Cyclo(Pro-Val)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TCI Chemical
Product number
C3893
Product name
Cyclo(L-Pro-L-Val)
Purity
min. 95.0 %
Packaging
25MG
Price
$73
Updated
2025/07/31
Cayman Chemical
Product number
27961
Product name
Cyclo(L-Pro-L-Val)
Packaging
25mg
Price
$37
Updated
2024/03/01
Cayman Chemical
Product number
27961
Product name
Cyclo(L-Pro-L-Val)
Packaging
50mg
Price
$68
Updated
2024/03/01
Cayman Chemical
Product number
27961
Product name
Cyclo(L-Pro-L-Val)
Packaging
100mg
Price
$129
Updated
2024/03/01
Cayman Chemical
Product number
27961
Product name
Cyclo(L-Pro-L-Val)
Packaging
250mg
Price
$283
Updated
2024/03/01
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CYCLO(-PRO-VAL) Chemical Properties,Usage,Production

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.

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.

Uses

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.

Definition

ChEBI: Cyclo(L-Pro-L-Val) is a piperazinone. It has a role as a metabolite.

References

[1] FRANCIS J. SCHMIDTZ. Metabolites from the marine sponge Tedania ignis. A new atisanediol and several known diketopiperazines[J]. The Journal of Organic Chemistry, 1983, 48 22: 3941-3945. DOI: 10.1021/jo00170a011
[2] CHRISTIANE BRACK  Frieder S  Annett Mikolasch. 2,5-Diketopiperazines Produced by Bacillus pumilus During Bacteriolysis of Arthrobacter citreus[J]. Marine Biotechnology, 2014, 16 4: 385-395. DOI: 10.1007/s10126-014-9559-y
[3] BAHAA EL-DIEN M. EL-GENDY  Mostafa E R. Antibacterial activity of diketopiperazines isolated from a marine fungus using t-butoxycarbonyl group as a simple tool for purification[J]. Bioorganic & Medicinal Chemistry Letters, 2015, 25 16: Pages 3125-3128. DOI: 10.1016/j.bmcl.2015.06.010
[4] M T HOLDEN. Quorum-sensing cross talk: isolation and chemical characterization of cyclic dipeptides from Pseudomonas aeruginosa and other gram-negative bacteria.[J]. Molecular Microbiology, 1999, 33 6: 1254-1266. DOI: 10.1046/j.1365-2958.1999.01577.x

CYCLO(-PRO-VAL) Preparation Products And Raw materials

Raw materials

Preparation Products

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2854-40-2, CYCLO(-PRO-VAL)Related Search:


  • CYCLO(-PRO-VAL)
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  • 2854-40-2