A bacterial metabolite
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Cyclo(L-Phe-L-Val)

Item No. 24943

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3S-(1-methylethyl)-6S-(phenylmethyl)-2,5-piperazinedione
CAS Number
35590-86-4
Synonyms
  • DKP101516
Molecular Formula
C14H18N2O2
Formula Weight
246.3
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
O=C([C@H](C(C)C)N1)N[C@@H](CC2=CC=CC=C2)C1=O
InChi Code
InChI=1S/C14H18N2O2/c1-9(2)12-14(18)15-11(13(17)16-12)8-10-6-4-3-5-7-10/h3-7,9,11-12H,8H2,1-2H3,(H,15,18)(H,16,17)/t11-,12-/m0/s1
InChi Key
OQQPOHUVAQPSHJ-RYUDHWBXSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    5 mg

    $267

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    25 mg

    $1,062

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    Cayman Chemical
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    Product Description

    Cyclo(L-Phe-L-Val) is a metabolite of the sponge bacterium Pseudoalteromonas sp. NJ6-3-1 that can autoinduce production of antibacterial substances active against S. aureus when co-cultured at a low cell density.1 It induces neurite outgrowth and branching of chick cortical neurons in vitro when used at concentrations of 16 and 32 µM.2 It increases phosphorylation of the PI3K substrate Akt, and neurite outgrowth induced by cyclo(L-Phe-L-Val) can be blocked by the PI3K inhibitor LY294002 (Item No. 70920). Cyclo(L-Phe-L-Val) enhances axon sprouting of calcitonin gene-related protein positive (CGRP+) primary afferents in the spinal cord following crush injury and of serotonin neurons in uninjured spinal cord. Cyclo(L-Phe-L-Val) is also a bitter taste component of cocoa and roasted coffee.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Guo, X., Zheng, L., Zhou, W., et al. 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. Ann. Microbiol. 61(2), 247-255 (2011).

    2. Wong, J.W., McPhail, L.T., Brastianos, H.C., et al. A novel diketopiperazine stimulates sprouting of spinally projecting axons. Exp. Neurol. 214(2), 331-340 (2008).

    3. Ginz, M., and Engelhardt, U.H. Identification of new diketopiperazines in roasted coffee. Eur. Food Res. Technol. 213(1), 8-11 (2001).