A diketopiperazine
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Cyclo(L-Pro-L-Val)

Item No. 27961

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3S,8aS)-hexahydro-3-(1-methylethyl)-pyrrolo[1,2-a]pyrazine-1,4-dione
CAS Number
2854-40-2
Synonyms
  • Cyclo(L-prolyl-L-valine)
Molecular Formula
C10H16N2O2
Formula Weight
196.2
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): 3 mg/mL
SMILES
O=C([C@H](C(C)C)N1)N2[C@](CCC2)([H])C1=O
InChi Code
InChI=1S/C10H16N2O2/c1-6(2)8-10(14)12-5-3-4-7(12)9(13)11-8/h6-8H,3-5H2,1-2H3,(H,11,13)/t7-,8-/m0/s1
InChi Key
XLUAWXQORJEMBD-YUMQZZPRSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 mg

    $41

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    50 mg

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    100 mg

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    250 mg

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    Cayman Chemical
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    Product 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.1,2,3 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).3 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 CV026.4 However, it does not activate or inhibit lacZ-based reporter fusions in S. liquefaciens or A. tumefaciens.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Schmitz, F.J., Vanderah, D.J., Hollenbeak, K.H., et al. Metabolites from the marine sponge Tedania ignis. A new atisanediol and several known diketopiperazines. The Journal of Organic Chemistry 48(22), 3941-3945 (1983).

    2. Brack, C., Mikolasch, A., and Schauer, F. 2,5-Diketopiperazines produced by Bacillus pumilus during bacteriolysis of Arthrobacter citreus. Mar. Biotechnol. (NY) 16(4), 385-395 (2014).

    3. El-Gendy, B.E.-D.M., and Rateb, M.E. Antibacterial activity of diketopiperazines isolated from a marine fungus using t-butoxycarbonyl group as a simple tool for purification. Bioorg. Med. Chem. Lett. 25(16), 3125-3128 (2015).

    4. Holden, M.T.G., Chhabra, S.R., de Nys, R., et al. Quorum-sensing cross talk: Isolation and chemical characterization of cyclic dipeptides from Pseudomonas aeruginosa and other gram-negative bacteria. Mol. Microbiol. 33(6), 1254-1266 (1999).