cyclo(L-Phe-L-Val)

cyclo(L-Phe-L-Val)

$200.00 - 5 mg

$700.00 - 25 mg

All prices in Australian dollars

Code
BIA-C1709
Synonyms
(3S,6S)-3-(1-Methylethyl)-6-(phenylmethyl)-2,5-piperazinedione; Cyclo(Phe-Val); DKP 101516
CAS #
35590-86-4
Molecular Formula
C14H18N2O2
Molecular Weight
246.3
Purity
>95% by HPLC
Long Term Storage
-20°C
Solubility
Soluble in ethanol, methanol, DMF or DMSO.

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Application Notes

Cyclo(L-Phe-L-Val) is a diketopiperazine metabolite first isolated from a marine bacteria, Pseudoalteromonas sp. in 2011. Cyclo(L-Phe-L-Val) is also produced as a secondary metabolite of Streptomyces rutgerensis and Bacillus subtilis. Limited bioassay data suggests cyclo(L-Phe-L-Val) acts as a quorum sensing regulator but does not itself exhibit antimicrobial activity. Exogenously added cyclo(L-Phe-L-Val) may induce Pseudoalteromonas sp. to produce antibacterial products under low cell density conditions. It appears to act by stimulating the bacteria to induce metabolite production.

References

  • A case study on chemical defense based on quorum sensing: antibacterial activity of sponge-associated bacterium Pseudoalteromonas sp. NJ6-3-1 induced by quorum sensing mechanisms. Guo X. et al., Ann. Microbiol. 2011, 61, 247.
  • Two new cyclic tetrapeptides of Streptomyces rutgersensis T009 isolated from Elaphodus davidianus excrement. Li S-Q et al., Helv. Chim. Acta 2016, 99, 210.

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