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Cyclo(L-Phe-L-Pro)

CAS# 3705-26-8

Cyclo(L-Phe-L-Pro)

Catalog No. BCN4029----Order now to get a substantial discount!

Product Name & Size Price Stock
Cyclo(L-Phe-L-Pro): 5mg $184 In Stock
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Quality Control of Cyclo(L-Phe-L-Pro)

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Chemical structure

Cyclo(L-Phe-L-Pro)

3D structure

Chemical Properties of Cyclo(L-Phe-L-Pro)

Cas No. 3705-26-8 SDF Download SDF
PubChem ID 443440 Appearance Oil
Formula C14H16N2O2 M.Wt 244.3
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (3S,8aS)-3-benzyl-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
SMILES C1CC2C(=O)NC(C(=O)N2C1)CC3=CC=CC=C3
Standard InChIKey QZBUWPVZSXDWSB-RYUDHWBXSA-N
Standard InChI InChI=1S/C14H16N2O2/c17-13-12-7-4-8-16(12)14(18)11(15-13)9-10-5-2-1-3-6-10/h1-3,5-6,11-12H,4,7-9H2,(H,15,17)/t11-,12-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Cyclo(L-Phe-L-Pro)

The Phellinus igniarius

Biological Activity of Cyclo(L-Phe-L-Pro)

Description1. Cyclo(L-Phe-L-Pro) shows antifungal and broad spectrum antibacterial activities. 2. Cyclo-(L-Phe-L-Pro) exhibits activity against methicillin-resistant S. aureus ATCC 43300 and Enterococcus raffinosus, with low toxicity against human hepatoma HepaRG cells.
TargetsAntifection

Cyclo(L-Phe-L-Pro) Dilution Calculator

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Cyclo(L-Phe-L-Pro) Molarity Calculator

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Preparing Stock Solutions of Cyclo(L-Phe-L-Pro)

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.0933 mL 20.4666 mL 40.9333 mL 81.8666 mL 102.3332 mL
5 mM 0.8187 mL 4.0933 mL 8.1867 mL 16.3733 mL 20.4666 mL
10 mM 0.4093 mL 2.0467 mL 4.0933 mL 8.1867 mL 10.2333 mL
50 mM 0.0819 mL 0.4093 mL 0.8187 mL 1.6373 mL 2.0467 mL
100 mM 0.0409 mL 0.2047 mL 0.4093 mL 0.8187 mL 1.0233 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Cyclo(L-Phe-L-Pro)

Isolation, Purification, and Characterization of Five Active Diketopiperazine Derivatives from Endophytic Streptomyces SUK 25 with Antimicrobial and Cytotoxic Activities.[Pubmed:28535606]

J Microbiol Biotechnol. 2017 Jul 28;27(7):1249-1256.

In our search for new sources of bioactive secondary metabolites from Streptomyces sp., the ethyl acetate extracts from endophytic Streptomyces SUK 25 afforded five active diketopiperazine (DKP) compounds. The aim of this study was to characterize the bioactive compounds isolated from endophytic Streptomyces SUK 25 and evaluate their bioactivity against multiple drug resistance (MDR) bacteria such as Enterococcus raffinosus, Staphylococcus aureus, Klebsiella pneumoniae, Acinetobacter baumanii, Pseudomonas aeruginosa, and Enterobacter spp., and their cytotoxic activities against the human hepatoma (HepaRG) cell line. The production of secondary metabolites by this strain was optimized through Thornton's medium. Isolation, purification, and identification of the bioactive compounds were carried out using high-performance liquid chromatography, high-resolution mass liquid chromatography-mass spectrometry, Fourier transform infrared spectroscopy, and nuclear magnetic resonance, and cryopreserved HepaRG cells were selected to test the cytotoxicity. The results showed that endophytic Streptomyces SUK 25 produces four active DKP compounds and an acetamide derivative, which were elucidated as cyclo-(L-Val-L-Pro), cyclo-(L-Leu-L-Pro), cyclo-(L-Phe-L-Pro), cyclo-(L-Val-L-Phe), and N-(7-hydroxy-6-methyl-octyl)-acetamide. These active compounds exhibited activity against methicillin-resistant S. aureus ATCC 43300 and Enterococcus raffinosus, with low toxicity against human hepatoma HepaRG cells. Endophytic Streptomyces SUK 25 has the ability to produce DKP derivatives biologically active against some MDR bacteria with relatively low toxicity against HepaRG cells line.

Lactobacillus plantarum MiLAB 393 produces the antifungal cyclic dipeptides cyclo(L-Phe-L-Pro) and cyclo(L-Phe-trans-4-OH-L-Pro) and 3-phenyllactic acid.[Pubmed:12200282]

Appl Environ Microbiol. 2002 Sep;68(9):4322-7.

We have isolated a Lactobacillus plantarum strain (MiLAB 393) from grass silage that produces broad-spectrum antifungal compounds, active against food- and feed-borne filamentous fungi and yeasts in a dual-culture agar plate assay. Fusarium sporotrichioides and Aspergillus fumigatus were the most sensitive among the molds, and Kluyveromyces marxianus was the most sensitive yeast species. No inhibitory activity could be detected against the mold Penicillium roqueforti or the yeast Zygosaccharomyces bailii. An isolation procedure, employing a microtiter well spore germination bioassay, was devised to isolate active compounds from culture filtrate. Cell-free supernatant was fractionated on a C(18) SPE column, and the 95% aqueous acetonitrile fraction was further separated on a preparative HPLC C(18) column. Fractions active in the bioassay were then fractionated on a porous graphitic carbon column. The structures of the antifungal compounds Cyclo(L-Phe-L-Pro), cyclo(L-Phe-trans-4-OH-L-Pro) and 3-phenyllactic acid (L/D isomer ratio, 9:1), were determined by nuclear magnetic resonance spectroscopy, mass spectrometry, and gas chromatography. MIC values against A. fumigatus and P. roqueforti were 20 mg ml(-1) for Cyclo(L-Phe-L-Pro) and 7.5 mg ml(-1) for phenyllactic acid. Combinations of the antifungal compounds revealed weak synergistic effects. The production of the antifungal cyclic dipeptides Cyclo(L-Phe-L-Pro) and cyclo(L-Phe-trans-4-OH-L-Pro) by lactic acid bacteria is reported here for the first time.

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