Cyclo(Pro-Pro)

CAS# 6708-06-1

Cyclo(Pro-Pro)

Catalog No. BCN2415----Order now to get a substantial discount!

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Cyclo(Pro-Pro): 5mg $184 In Stock
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Quality Control of Cyclo(Pro-Pro)

Number of papers citing our products

Chemical structure

Cyclo(Pro-Pro)

3D structure

Chemical Properties of Cyclo(Pro-Pro)

Cas No. 6708-06-1 SDF Download SDF
PubChem ID 529063 Appearance Powder
Formula C10H14N2O2 M.Wt 194.23
Type of Compound Miscellaneous Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 1,2,3,5a,6,7,8,10a-octahydrodipyrrolo[1,2-c:1',2'-f]pyrazine-5,10-dione
SMILES C1CC2C(=O)N3CCCC3C(=O)N2C1
Standard InChIKey BKASXWPLSXFART-UHFFFAOYSA-N
Standard InChI InChI=1S/C10H14N2O2/c13-9-7-3-1-5-11(7)10(14)8-4-2-6-12(8)9/h7-8H,1-6H2
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-Pro)

The Nigrospora sp.Z18-17

Biological Activity of Cyclo(Pro-Pro)

DescriptionCyclo(Pro-Pro) tasted bitter.Verpacamides A-D, a sequence of C11N5 diketopiperazines relating cyclo(Pro-Pro) to cyclo(Pro-Arg), from the marine sponge Axinella vaceleti is possible biogenetic precursors of pyrrole-2-aminoimidazole alkaloids.

Protocol of Cyclo(Pro-Pro)

Structure Identification
Anal Bioanal Chem. 2014 Apr;406(9-10):2433-44.

Quantification of cyclic dipeptides from cultures of Lactobacillus brevis R2Δ by HRGC/MS using stable isotope dilution assay.[Pubmed: 24477717 ]

Lactic acid bacteria (LAB) play an important role as natural preservatives in fermented food and beverage systems, reducing the application of chemical additives. Thus, investigating their antifungal compounds, such as cyclic dipeptides, has gained prominence. Previous research has primarily focussed on isolation of these compounds. However, their precise quantification will provide further information regarding their antifungal performance in a complex system.
METHODS AND RESULTS:
To address this, deuterated labelled standards of the cyclic dipeptides cyclo(Leu-Pro), Cyclo(Pro-Pro), cyclo(Met-Pro) and cyclo(Phe-Pro) were synthesized, and stable isotope dilution assays were developed, enabling an accurate quantification of cyclo(Leu-Pro), Cyclo(Pro-Pro), cyclo(Met-Pro) and cyclo(Phe-Pro) in MRS-broth and wort. Quantitative results showed that, in the Lactobacillus brevis R2Δ fermented MRS-broth, the concentrations of cyclo(Leu-Pro), Cyclo(Pro-Pro) and cyclo(Phe-Pro) were significantly higher (P < 0.05), than in wort for cyclo (Leu-Pro) when compared with their controls.
CONCLUSIONS:
This indicates that the formation of these three cyclic dipeptides is related to L. brevis R2Δ metabolism. Furthermore, this represents the first report of cyclic dipeptides quantification using stable isotope dilution assays in LAB cultures both in vitro and in a food system.

Org .Lett., 2006, 8(11):2421-4.

Verpacamides A-D, a sequence of C11N5 diketopiperazines relating cyclo(Pro-Pro) to cyclo(Pro-Arg), from the marine sponge Axinella vaceleti: possible biogenetic precursors of pyrrole-2-aminoimidazole alkaloids.[Pubmed: 16706541 ]

Four C(11)N(5) diketopiperazine metabolites named verpacamides A (6), B (7), C (8), and D (9) consisting of a proline-arginine dipeptide skeleton have been isolated from the marine sponge Axinella vaceleti. Verpacamides A-D are a sequence of metabolites showing the transformation of proline and arginine into the oxidized guanidinyl-Cyclo(Pro-Pro) 8 and 9. Compounds 6-9 are structurally and chemically related to C(11)N(5) pyrrole-2-aminoimidazole metabolites also isolated from the Axinellidae and Agelasidae families of sponges and exemplified by dispacamide A (4) and dibromophakellin (10).

Cyclo(Pro-Pro) Dilution Calculator

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Cyclo(Pro-Pro) Molarity Calculator

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Preparing Stock Solutions of Cyclo(Pro-Pro)

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 5.1485 mL 25.7427 mL 51.4854 mL 102.9707 mL 128.7134 mL
5 mM 1.0297 mL 5.1485 mL 10.2971 mL 20.5941 mL 25.7427 mL
10 mM 0.5149 mL 2.5743 mL 5.1485 mL 10.2971 mL 12.8713 mL
50 mM 0.103 mL 0.5149 mL 1.0297 mL 2.0594 mL 2.5743 mL
100 mM 0.0515 mL 0.2574 mL 0.5149 mL 1.0297 mL 1.2871 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-Pro)

Quantification of cyclic dipeptides from cultures of Lactobacillus brevis R2Delta by HRGC/MS using stable isotope dilution assay.[Pubmed:24477717]

Anal Bioanal Chem. 2014 Apr;406(9-10):2433-44.

Lactic acid bacteria (LAB) play an important role as natural preservatives in fermented food and beverage systems, reducing the application of chemical additives. Thus, investigating their antifungal compounds, such as cyclic dipeptides, has gained prominence. Previous research has primarily focussed on isolation of these compounds. However, their precise quantification will provide further information regarding their antifungal performance in a complex system. To address this, deuterated labelled standards of the cyclic dipeptides cyclo(Leu-Pro), Cyclo(Pro-Pro), cyclo(Met-Pro) and cyclo(Phe-Pro) were synthesized, and stable isotope dilution assays were developed, enabling an accurate quantification of cyclo(Leu-Pro), Cyclo(Pro-Pro), cyclo(Met-Pro) and cyclo(Phe-Pro) in MRS-broth and wort. Quantitative results showed that, in the Lactobacillus brevis R2Delta fermented MRS-broth, the concentrations of cyclo(Leu-Pro), Cyclo(Pro-Pro) and cyclo(Phe-Pro) were significantly higher (P < 0.05), than in wort for cyclo (Leu-Pro) when compared with their controls. This indicates that the formation of these three cyclic dipeptides is related to L. brevis R2Delta metabolism. Furthermore, this represents the first report of cyclic dipeptides quantification using stable isotope dilution assays in LAB cultures both in vitro and in a food system.

Verpacamides A-D, a sequence of C11N5 diketopiperazines relating cyclo(Pro-Pro) to cyclo(Pro-Arg), from the marine sponge Axinella vaceleti: possible biogenetic precursors of pyrrole-2-aminoimidazole alkaloids.[Pubmed:16706541]

Org Lett. 2006 May 25;8(11):2421-4.

[reaction: see text] Four C(11)N(5) diketopiperazine metabolites named verpacamides A (6), B (7), C (8), and D (9) consisting of a proline-arginine dipeptide skeleton have been isolated from the marine sponge Axinella vaceleti. Verpacamides A-D are a sequence of metabolites showing the transformation of proline and arginine into the oxidized guanidinyl-Cyclo(Pro-Pro) 8 and 9. Compounds 6-9 are structurally and chemically related to C(11)N(5) pyrrole-2-aminoimidazole metabolites also isolated from the Axinellidae and Agelasidae families of sponges and exemplified by dispacamide A (4) and dibromophakellin (10).

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