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Calystegine A3

CAS# 131580-36-4

Calystegine A3

Catalog No. BCN1884----Order now to get a substantial discount!

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Quality Control of Calystegine A3

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Chemical structure

Calystegine A3

3D structure

Chemical Properties of Calystegine A3

Cas No. 131580-36-4 SDF Download SDF
PubChem ID 442999 Appearance Powder
Formula C7H13NO3 M.Wt 159.18
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (3R,4R)-8-azabicyclo[3.2.1]octane-3,4,5-triol
SMILES C1CC2(C(C(CC1N2)O)O)O
Standard InChIKey XOCBOVUINUHZJA-RKXXOXFUSA-N
Standard InChI InChI=1S/C7H13NO3/c9-5-3-4-1-2-7(11,8-4)6(5)10/h4-6,8-11H,1-3H2/t4?,5-,6-,7?/m1/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 Calystegine A3

The leaves of Morus alba L.

Biological Activity of Calystegine A3

Description1. Calystegines A3 and B2 can effectively stabilize β-glucocerebrosidase, and consequently increase intracellular β-glucocerebrosidase activities in N370S fibroblasts. 2. Calystegines A3, B2, and C1 are glycosidase inhibitors.

Calystegine A3 Dilution Calculator

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Calystegine A3 Molarity Calculator

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Preparing Stock Solutions of Calystegine A3

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 6.2822 mL 31.411 mL 62.822 mL 125.6439 mL 157.0549 mL
5 mM 1.2564 mL 6.2822 mL 12.5644 mL 25.1288 mL 31.411 mL
10 mM 0.6282 mL 3.1411 mL 6.2822 mL 12.5644 mL 15.7055 mL
50 mM 0.1256 mL 0.6282 mL 1.2564 mL 2.5129 mL 3.1411 mL
100 mM 0.0628 mL 0.3141 mL 0.6282 mL 1.2564 mL 1.5705 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 Calystegine A3

Docking and SAR studies of calystegines: binding orientation and influence on pharmacological chaperone effects for Gaucher's disease.[Pubmed:24657053]

Bioorg Med Chem. 2014 Apr 15;22(8):2435-41.

We report on the identification of the required configuration and binding orientation of nor-tropane alkaloid calystegines against beta-glucocerebrosidase. Calystegine B2 is a potent competitive inhibitor of human lysosomal beta-glucocerebrosidase with Ki value of 3.3 muM. A molecular docking study revealed that calystegine B2 had a favorable van der Waals interactions (Phe128, Trp179, and Phe246) and the hydrogen bonding (Glu235, Glu340, Asp127, Trp179, Asn234, Trp381 and Asn396) was similar to that of isofagomine. All calystegine isomers bound into the same active site as calystegine B2 and the essential hydrogen bonds formed to Asp127, Glu235 and Glu340 were maintained. However, their binding orientations were obviously different. Calystegine A3 bound to beta-glucocerebrosidase with the same orientations as calystegine B2 (Type 1), while calystegine B3 and B4 had different binding orientations (Type 2). It is noteworthy that Type 1 orientated calystegines B2 and A3 effectively stabilized beta-glucocerebrosidase, and consequently increased intracellular beta-glucocerebrosidase activities in N370S fibroblasts, while Type 2 orientated calystegines B3 and B4 could not keep the enzyme activity. These results clearly indicate that the binding orientations of calystegines are changed by the configuration of the hydroxyl groups on the nor-tropane ring and the suitable binding orientation is a requirement for achieving a strong affinity to beta-glucocerebrosidase.

The comparative pathology of the glycosidase inhibitors swainsonine, castanospermine, and calystegines A3, B2, and C1 in mice.[Pubmed:18497426]

Toxicol Pathol. 2008 Jul;36(5):651-9.

To study various polyhydroxy-alkaloid glycosidase inhibitors, 16 groups of 3 mice were dosed using osmotic minipumps with swainsonine (0, 0.1, 1, and 10 mg/kg/day), castanospermine, and calystegines A(3), B(2), and C(1) (1, 10, and 100 mg/kg/day). After 28 days, the mice were euthanized, necropsied, and examined using light and electron microscopy. The high-dose swainsonine-treated mice developed neurologic disease with neuro-visceral vacuolation typical of locoweed poisoning. Castanospermine- and calystegines-treated mice were clinically normal; however, high-dose castanospermine-treated mice had thyroid, renal, hepatic, and skeletal myocyte vacuolation. Histochemically, swainsonine- and castanospermine-induced vacuoles contained mannose-rich oligosaccharides. High-dose calystegine A(3)-treated mice had increased numbers of granulated cells in the hepatic sinusoids. Electron microscopy, lectin histochemistry, and immunohistochemistry suggest these are pit cells (specialized NK cells). Histochemically, the granules contain glycoproteins or oligosaccharides with abundant terminal N-acetylglucosamine residues. Other calystegine-treated mice were histologically normal. These findings indicate that swainsonine produced lesions similar to locoweed, castanospermine caused vacuolar changes with minor changes in glycogen metabolism, and only calystegine A(3) produced minimal hepatic changes. These also suggest that in mice calystegines and castanospermine are less toxic than swainsonine, and as rodents are relatively resistant to disease, they are poor models to study such induced storage diseases.

Chiral pool synthesis of calystegine A3 from 2-deoxyglucose via a Brown allylation.[Pubmed:22088883]

Carbohydr Res. 2011 Dec 27;346(18):2855-61.

Calystegine A(3) is a naturally occurring nortropane iminosugar of which there previously have been three total syntheses. Inspired by our previous work we here report on a fourth approach using 17 steps from 2-deoxy-d-glucose applying a diastereoselective allylation protocol.

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