A bacterial cyclic dipeptide
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Cyclo(Δ-Ala-L-Val)

Item No. 25739

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-methylene-6S-(1-methylethyl)-2,5-piperazinedione
CAS Number
25516-00-1
Molecular Formula
C8H12N2O2
Formula Weight
168.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: solubleDMSO: solubleEthanol: solubleMethanol: soluble
SMILES
O=C(C(N1)=C)N[C@@H](C(C)C)C1=O
InChi Code
InChI=1S/C8H12N2O2/c1-4(2)6-8(12)9-5(3)7(11)10-6/h4,6H,3H2,1-2H3,(H,9,12)(H,10,11)/t6-/m0/s1
InChi Key
NFYRGJUKSGFWQF-LURJTMIESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $181

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    5 mg

    $852

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    Cayman Chemical
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    Product Description

    Cyclo(Δ-Ala-L-Val) is a bacterial cyclic dipeptide characterized as a diketopiperazine.1 It activates a LuxR-based N-acylhomoserine lactone (AHL) E. coli biosensor and blocks activation of the biosensor by the quorum sensing signal molecule N-(β-ketocaproyl)-L-homoserine lactone (3-oxo-C6-HSL; Item No. 10011207) with an IC50 value of 0.8 mM. Cyclo(Δ-Ala-L-Val) (15 μM) reduces S. liquefaciens colony expansion by 21%, indicating inhibition of swarming motility. It also inhibits the interaction of the kinases Ras and Raf-1 in a yeast two-hybrid assay in a concentration-dependent manner.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).

    2. Cheenpracha, S., Borris, R.P., Tran, T.T., et al. Three new amides from Streptomyces sp. H7372. J. Braz. Chem. Soc. 22(2), 223-229 (2011).