Cyclo(Pro-Val)

CAS# 5654-87-5

Cyclo(Pro-Val)

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Chemical structure

Cyclo(Pro-Val)

3D structure

Chemical Properties of Cyclo(Pro-Val)

Cas No. 5654-87-5 SDF Download SDF
PubChem ID 98951 Appearance Powder
Formula C10H16N2O2 M.Wt 196.25
Type of Compound Miscellaneous Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 3-propan-2-yl-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
SMILES CC(C)C1C(=O)N2CCCC2C(=O)N1
Standard InChIKey XLUAWXQORJEMBD-UHFFFAOYSA-N
Standard InChI InChI=1S/C10H16N2O2/c1-6(2)8-10(14)12-5-3-4-7(12)9(13)11-8/h6-8H,3-5H2,1-2H3,(H,11,13)
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(Pro-Val)

The Penicillium oxalicum

Biological Activity of Cyclo(Pro-Val)

DescriptionCyclo(Pro-Val) shows cyctoxic, moderate antifungal and weak antitumor activities in vitro, it can inhibit the growth of Bacillus subtilis with the minimal inhibitory concentration (MIC) value of 0.8 g/L. Cyclo(Pro-Val) and cyclo(Pro-Tyr) are toxic to both suspension cells and seedlings of Pinus thunbergii, which may offer some clues to research the mechanism of pine wilt disease caused by pine wood nematode.
TargetsAntifection
In vitro

Cyclic dipeptide constituents from the mangrove fungus Penicillium oxalicum(No.092007).[Reference: WebLink]

Journal of Shenyang Pharmaceutical University, 2007,24(8) :474-8.

To study the metabolites of mangrove fungus Penicillium oxalicum from the south China sea and search for new anti-tumor compounds.
METHODS AND RESULTS:
Compounds were isolated by silica gel,ODS column chromatography,Sephadex LH-20 column chromatography and reversed-phase HPLC purification.Structural elucidation was achieved by physico-chemical constants and spectroscopic analysis.MTT assay was used to evaluate the bioactivities in vitro. Six cyclic dipeptides were isolated from the acetone extracts of mycelium of fungus and elucidated as cyclo-(Phe-Ile)(1),cyclo-(Phe-Val)(3),cyclo-(Ile-Leu)(3),cyclo-(Val-Val)(4),Cyclo(Pro-Val)(5),cyclo-(Pro-Gly)(6).Coumpouds 2,3 and 5 could evidently inhibit the growth of cancer cell lines HepG Ⅱ and LNCaP at the concentration of 50 μg·mL-1.
CONCLUSIONS:
All of Compounds are obtained from the marine fungus for the fist time.Compounds 2,3 and 5 show cytotoxic activity in vitro.

Antifungal cyclopeptides from Halobacillus litoralis YS3106 of marine origin.[Reference: WebLink]

Tetrahedron Lett.,2002, 33(51):6545-8.


METHODS AND RESULTS:
Three new cyclopeptides, including halolitoralin A (a cyclic hexapeptide), halolitoralin B and C (two cyclic tetrapeptides), together with three known cyclic dipeptides, Cyclo(Pro-Val), cyclo(Pro-Leu) and cyclo(Ile-Val) were isolated from the ferment broth of a marine sediment-derived Halobacillus litoralis YS3106.
CONCLUSIONS:
The cyclopeptides show surprisingly simple architectures with highly repeated residue units, which showed moderate antifungal and weak antitumor activities in vitro.

Protocol of Cyclo(Pro-Val)

Structure Identification
J Nematol. 2007 Sep;39(3):243-7.

Two Cyclic Dipeptides from Pseudomonas fluorescens GcM5-1A Carried by the Pine Wood Nematode and Their Toxicities to Japanese Black Pine Suspension Cells and Seedlings in vitro.[Pubmed: 19259494]

Pseudomonas fluorescens GcM5-1A, isolated from the pine wood nematode (PWN), Bursaphelenchus xylophilus, was cultured in Luria Broth medium (LB).
METHODS AND RESULTS:
The clarified culture was extracted with ethyl acetate, and two dipeptides were purified from the extract. The chemical structures of 1 and 2 were identified as Cyclo(Pro-Val)and cyclo(-Pro-Tyr-), respectively, by MS, (1)H NMR, (13)C NMR,(1)H-(1)H COSY, 1H -(13)C COSY spectra.
CONCLUSIONS:
Bioassay results showed that the two compounds were toxic to both suspension cells and seedlings of Pinus thunbergii, which may offer some clues to research the mechanism of pine wilt disease caused by PWN.

Cyclo(Pro-Val) Dilution Calculator

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Cyclo(Pro-Val) Molarity Calculator

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Preparing Stock Solutions of Cyclo(Pro-Val)

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 5.0955 mL 25.4777 mL 50.9554 mL 101.9108 mL 127.3885 mL
5 mM 1.0191 mL 5.0955 mL 10.1911 mL 20.3822 mL 25.4777 mL
10 mM 0.5096 mL 2.5478 mL 5.0955 mL 10.1911 mL 12.7389 mL
50 mM 0.1019 mL 0.5096 mL 1.0191 mL 2.0382 mL 2.5478 mL
100 mM 0.051 mL 0.2548 mL 0.5096 mL 1.0191 mL 1.2739 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(Pro-Val)

Two Cyclic Dipeptides from Pseudomonas fluorescens GcM5-1A Carried by the Pine Wood Nematode and Their Toxicities to Japanese Black Pine Suspension Cells and Seedlings in vitro.[Pubmed:19259494]

J Nematol. 2007 Sep;39(3):243-7.

Pseudomonas fluorescens GcM5-1A, isolated from the pine wood nematode (PWN), Bursaphelenchus xylophilus, was cultured in Luria Broth medium (LB). The clarified culture was extracted with ethyl acetate, and two dipeptides were purified from the extract. The chemical structures of 1 and 2 were identified as cyclo(-Pro-Val-)and cyclo(-Pro-Tyr-), respectively, by MS, (1)H NMR, (13)C NMR,(1)H-(1)H COSY, 1H -(13)C COSY spectra. Bioassay results showed that the two compounds were toxic to both suspension cells and seedlings of Pinus thunbergii, which may offer some clues to research the mechanism of pine wilt disease caused by PWN.

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