Cyclo(Phe-Gly)

CAS# 5037-75-2

Cyclo(Phe-Gly)

Catalog No. BCN2431----Order now to get a substantial discount!

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Quality Control of Cyclo(Phe-Gly)

Number of papers citing our products

Chemical structure

Cyclo(Phe-Gly)

3D structure

Chemical Properties of Cyclo(Phe-Gly)

Cas No. 5037-75-2 SDF Download SDF
PubChem ID 138409 Appearance Powder
Formula C11H12N2O2 M.Wt 204.23
Type of Compound Miscellaneous Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 3-benzylpiperazine-2,5-dione
SMILES C1C(=O)NC(C(=O)N1)CC2=CC=CC=C2
Standard InChIKey UZOJHXFWJFSFAI-UHFFFAOYSA-N
Standard InChI InChI=1S/C11H12N2O2/c14-10-7-12-11(15)9(13-10)6-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,12,15)(H,13,14)
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(Phe-Gly)

The Pantoea agglomerans

Biological Activity of Cyclo(Phe-Gly)

DescriptionCyclo(Phe-Gly) shows weak antagonistic activity against VEGFR2 -CD, it also shows strong inhibitory activity against human cancer cells(KB,KBv200) with LD50 at 6.5 and 11.2 umol/L,respectively.
TargetsIFN-γ | IL Receptor | HSP (e.g. HSP90) | VEGFR
In vitro

Discovery on antagonists of VEGFR2-CD produced by Streptomyces strain I06A-02832[Reference: WebLink]

Chinese Journal of Antibiotics,2014,6:408-12,421.

To discover antagonists of VEGFR2-CD from the fermentation broth produced by streptomyces strain I06A-02832.
METHODS AND RESULTS:
Under the guidance of ELISA assay against VEGFR2-CD, Compounds 2832 B and 2832 C were isolated and purified by combination of different column chromatographies and HPLC. The structures of compounds 2832 B and C were identified by combination of analysis of UV, IR, MS and 1D-NMR, 2D-NMR. Compounds 2832 B and 2832 C were purified and structurally identified as cyclic dipeptides, and were the same with cyclo-(Pro-Tyr) and Cyclo(Phe-Gly) respectively. Compounds 2832 B and 2832 C showed weak antagonistic activity against VEGFR2-CD by ELISA assay.
CONCLUSIONS:
They are firstly reported compounds 2832 B and 2832 C had antagonistic activity against VEGFR2-CD.

Study on the Metabolites of Mangrove Endophytic Fungus GX-3 from the South China Sea[Reference: WebLink]

Hubei Agricultural Sciences, 2013, 52 (11) :2558- 61.


METHODS AND RESULTS:
The secondary metabolite compounds of mangrove endophytic fungus GX-3 from the South China Sea were isolated by column chromatography and identified on the basis of physic-chemical constants and spectral analysis.Six metabolites were obtained and elucidated as Cyclo(Phe-Gly) (1),cyclo-(Leu-Gly)(2),Fusaric acid(3),3,6-di-sec-butyl-1,4-dihydroxypiperazine-2,5-dione(4),cyclo-(pro-leu)(5),cyclo-(Gly-Leu)(6).
CONCLUSIONS:
In the preliminary bioassay,1 showed strong inhibitory activity against KB,KBv200 with LD50 at 6.5 and 11.2 μmol/L,respectively.The six metabolites were obtained from endophytic fungus GX-3 for the first time.

Protocol of Cyclo(Phe-Gly)

Animal Research

Enhancement of secondary metabolites from Bacillus Licheniformis XY-52 on immune response and expression of some immune-related genes in common carp, Cyprinus carpio.[Pubmed: 25703710]

Fish Shellfish Immunol. 2015 Jul;45(1):124-31.


METHODS AND RESULTS:
This study was undertaken to isolate active secondary metabolites from immunostimulatory Bacillus Licheniformis XY-52 and evaluate their activities at 0%, 0.5%, 1.0%, and 2.0% doses supplementation with feed on immune response in common carp at weeks 1, 2, and 3. By applying chromatography techniques and successive recrystallization, two purified metabolites were obtained and identified by spectral data (mass spectrometry and nuclear magnetic resonance) as: Cyclo(Phe-Tyr) and Cyclo(Phe-Gly). The results revealed that humoral innate immune parameters (lysozyme activity, phagocytic activity and bactericidal activity) were significantly (P < 0.05) increased after feeding on the two active compounds-supplemented diet. Furthermore, administration of the two active compounds significantly (P < 0.05) up regulated IL-1β, Type 1 IFN, IFN g2b, IL10 and TNF-α gene expression. Heat shock protein 70 (HSP70) gene expression was significantly (P < 0.05) lower as compared to control group at the end of trial. Common carp fed with the two compounds had higher survival rates (69.3%) compared to the controls (32.0%) after challenged with the pathogen, Aeromonas hydrophila.
CONCLUSIONS:
The present study indicates that the two isolated active compounds could positively influence immune response and enhance disease resistance of common carp against A. hydrophila infection.

Structure Identification
Nat Prod Commun. 2013 Dec;8(12):1753-4.

A new cyclopeptide from endophytic Streptomyces sp. YIM 64018.[Pubmed: 24555291]

One new cyclopeptide, cyclo(L-Phe-L-Ala-L-Phe-Gly), named as vinaceuline (1) and three known cyclodipeptides, Cyclo(Phe-Gly), cyclo(Phe-4-hydroxyl-Pro) and cyclo(Phe-Ile) were isolated from broth culture of endophytic Streptomyces YIM 64018 associated with Paraboea sinensis.
METHODS AND RESULTS:
The planar structure of the new compound was assigned on the basis of 1D and 2D NMR spectroscopic techniques, while t he a bsolute configurations of the amino acid residueswere determined by application of the advanced Marfey method.

CONCLUSIONS:
Cyclotetrapeptides are rarely found as Streptomycete metabolites.

Cyclo(Phe-Gly) Dilution Calculator

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Preparing Stock Solutions of Cyclo(Phe-Gly)

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.8964 mL 24.4822 mL 48.9644 mL 97.9288 mL 122.411 mL
5 mM 0.9793 mL 4.8964 mL 9.7929 mL 19.5858 mL 24.4822 mL
10 mM 0.4896 mL 2.4482 mL 4.8964 mL 9.7929 mL 12.2411 mL
50 mM 0.0979 mL 0.4896 mL 0.9793 mL 1.9586 mL 2.4482 mL
100 mM 0.049 mL 0.2448 mL 0.4896 mL 0.9793 mL 1.2241 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(Phe-Gly)

A new cyclopeptide from endophytic Streptomyces sp. YIM 64018.[Pubmed:24555291]

Nat Prod Commun. 2013 Dec;8(12):1753-4.

One new cyclopeptide, cyclo(L-Phe-L-Ala-L-Phe-Gly), named as vinaceuline (1) and three known cyclodipeptides, cyclo (Phe-Gly), cyclo (Phe-4-hydroxyl-Pro) and cyclo (Phe-Ile) were isolated from broth culture of endophytic Streptomyces YIM 64018 associated with Paraboea sinensis. The planar structure of the new compound was assigned on the basis of 1D and 2D NMR spectroscopic techniques, while t he a bsolute configurations of the amino acid residueswere determined by application of the advanced Marfey method. Cyclotetrapeptides are rarely found as Streptomycete metabolites.

Enhancement of secondary metabolites from Bacillus Licheniformis XY-52 on immune response and expression of some immune-related genes in common carp, Cyprinus carpio.[Pubmed:25703710]

Fish Shellfish Immunol. 2015 Jul;45(1):124-31.

This study was undertaken to isolate active secondary metabolites from immunostimulatory Bacillus Licheniformis XY-52 and evaluate their activities at 0%, 0.5%, 1.0%, and 2.0% doses supplementation with feed on immune response in common carp at weeks 1, 2, and 3. By applying chromatography techniques and successive recrystallization, two purified metabolites were obtained and identified by spectral data (mass spectrometry and nuclear magnetic resonance) as: Cyclo-(Phe-Tyr) and Cyclo-(Phe-Gly). The results revealed that humoral innate immune parameters (lysozyme activity, phagocytic activity and bactericidal activity) were significantly (P < 0.05) increased after feeding on the two active compounds-supplemented diet. Furthermore, administration of the two active compounds significantly (P < 0.05) up regulated IL-1beta, Type 1 IFN, IFN g2b, IL10 and TNF-alpha gene expression. Heat shock protein 70 (HSP70) gene expression was significantly (P < 0.05) lower as compared to control group at the end of trial. Common carp fed with the two compounds had higher survival rates (69.3%) compared to the controls (32.0%) after challenged with the pathogen, Aeromonas hydrophila. The present study indicates that the two isolated active compounds could positively influence immune response and enhance disease resistance of common carp against A. hydrophila infection.

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