Cyclo(L-Phe-L-Val)

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Cyclo(L-Phe-L-Val) Basic information
Product Name:Cyclo(L-Phe-L-Val)
Synonyms:Cyclo(L-Phe-L-Val);(3S,6S)-3-(1-methylethyl)-6-(phenylmethyl)piperazine-2,5-dione;Cyclo(-L-Val-L-Phe);2,5-Piperazinedione, 3-(1-methylethyl)-6-(phenylmethyl)-, (3S,6S)-;3S-(1-methylethyl)-6S-(phenylmethyl)-2,5-piperazinedione;(3S,6S)-3-benzyl-6-isopropylpiperazine-2,5-dione
CAS:35590-86-4
MF:C14H18N2O2
MW:246.3
EINECS:
Product Categories:
Mol File:35590-86-4.mol
Cyclo(L-Phe-L-Val) Structure
Cyclo(L-Phe-L-Val) Chemical Properties
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
pka13.12±0.60(Predicted)
color White to off-white
Safety Information
MSDS Information
Cyclo(L-Phe-L-Val) Usage And Synthesis
DescriptionCyclo(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.
UsesCyclo(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
Cyclo(L-Phe-L-Val) Preparation Products And Raw materials
Tag:Cyclo(L-Phe-L-Val)(35590-86-4) Related Product Information
Cyclo(-Pro-Val) 2,5-Piperazinedione, 3-(hydroxymethyl)-6-(1-methylethyl)-, (3S,6S)- cyclo(delta-Ala-L-Val) Pyrrolo(2,1-F)pyrazine-1,4-dione, 2,3,6,7,8,8A-hexahydro-3-(phenylmethyl)- Cyclo(Tyr-Val) Nystatin