| Identification | Back Directory | [Name]
Cyclo(L-Phe-L-Val) | [CAS]
35590-86-4 | [Synonyms]
Cyclo(L-Phe-L-Val)
Cyclo(-L-Val-L-Phe)
(3S,6S)-3-(1-methylethyl)-6-(phenylmethyl)piperazine-2,5-dione | [Molecular Formula]
C14H18N2O2 | [MDL Number]
MFCD33021199 | [MOL File]
35590-86-4.mol | [Molecular Weight]
246.3 |
| Chemical Properties | Back Directory | [Melting point ]
176-178 °C | [Boiling point ]
515.6±43.0 °C(Predicted) | [density ]
1.109±0.06 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
DMF: soluble; DMSO: soluble; Ethanol: soluble; Methanol: soluble | [form ]
A solid | [pka]
13.12±0.60(Predicted) | [color ]
White to off-white |
| Hazard Information | Back Directory | [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. It induces neurite outgrowth and branching of chick cortical neurons in vitro when used at concentrations of 16 and 32 μM. 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 . 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. | [Uses]
Cyclo(L-Phe-L-Val) is a potent inhibitor of enzymes isocitrate lyase (ICL) (IC50=27 μg/mL). cyclo(L-Phe-L-Val) inhibits the gene transcription of ICL in C. albicans under C2-carbon-utilizing conditions[1]. | [References]
[1] Kim H, et al. Inhibitory Effects of Diketopiperazines from Marine-Derived Streptomyces puniceus on the Isocitrate Lyase of Candida albicans. Molecules. 2019 Jun 4;24(11):2111. DOI:10.3390/molecules24112111 |
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