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Calystegine B2

CAS# 127414-85-1

Calystegine B2

Catalog No. BCN1879----Order now to get a substantial discount!

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Chemical structure

Calystegine B2

3D structure

Chemical Properties of Calystegine B2

Cas No. 127414-85-1 SDF Download SDF
PubChem ID 443000 Appearance Oil
Formula C7H13NO4 M.Wt 175.18
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (2S,3R,4R)-8-azabicyclo[3.2.1]octane-2,3,4,5-tetrol
SMILES C1CC2(C(C(C(C1N2)O)O)O)O
Standard InChIKey FXFBVZOJVHCEDO-NMACYSKISA-N
Standard InChI InChI=1S/C7H13NO4/c9-4-3-1-2-7(12,8-3)6(11)5(4)10/h3-6,8-12H,1-2H2/t3?,4-,5+,6+,7?/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 Calystegine B2

The root bark of Lycium chinense Mill.

Biological Activity of Calystegine B2

Description1. Calystegine B2 can inhibit the alpha-galactosidase and enzymes beta-glucosidase activities.

Calystegine B2 Dilution Calculator

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Calystegine B2 Molarity Calculator

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Preparing Stock Solutions of Calystegine B2

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 5.7084 mL 28.5421 mL 57.0841 mL 114.1683 mL 142.7104 mL
5 mM 1.1417 mL 5.7084 mL 11.4168 mL 22.8337 mL 28.5421 mL
10 mM 0.5708 mL 2.8542 mL 5.7084 mL 11.4168 mL 14.271 mL
50 mM 0.1142 mL 0.5708 mL 1.1417 mL 2.2834 mL 2.8542 mL
100 mM 0.0571 mL 0.2854 mL 0.5708 mL 1.1417 mL 1.4271 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 B2

Synthesis and evaluation of calystegine B2 analogues as glycosidase inhibitors.[Pubmed:11701011]

J Org Chem. 2001 Nov 16;66(23):7604-14.

A practical synthesis of polyhydroxylated 6-oxa-nor-tropanes incorporating the essential structural features of calystegine B(2) from 5-deoxy-5-thioureido and 5-ureido-L-idofuranose precursors is presented. The methodology relies on the ability of pseudoamide-type nitrogen atoms (thiourea, urea, and carbamate) to undergo nucleophilic addition to the masked aldehyde group of the monosaccharide. The generated hemiaminal functionality may further undergo in situ intramolecular glycosidation to give the bicyclic aminoacetal compounds, the whole process being favored by the anomeric effect. A series of derivatives bearing different substituents at nitrogen has been prepared and screened against several glycosidases in comparison with xylonojirimycin-type piperidine analogues. Interestingly, strong and highly specific inhibition of bovine liver beta-glucosidase was observed for 6-oxacalystegine B(2) analogues incorporating aromatic pseudoaglyconic groups. On the basis of these data, a 1-azasugar inhibition mode is proposed for this family of glycomimetics.

Biological activities of the nortropane alkaloid, calystegine B2, and analogs: structure-function relationships.[Pubmed:8988598]

J Nat Prod. 1996 Dec;59(12):1137-42.

Calystegines, polyhydroxy nortropane alkaloids, are a recently discovered group of plant secondary metabolites believed to influence rhizosphere ecology as nutritional sources for soil microorganisms and as glycosidase inhibitors. Evidence is presented that calystegines mediate nutritional relationships under natural conditions and that their biological activities are closely correlated with their chemical structures and stereochemistry. Assays using synthetic (+)- and (-)-enantiomers of Calystegine B2 established that catabolism by Rhizobium meliloti, glycosidase inhibition, and allelopathic activities were uniquely associated with the natural, (+)-enantiomer. Furthermore, the N-methyl derivative of Calystegine B2 was not catabolized by R. meliloti, and it inhibited alpha-galactosidase, but not beta-glucosidase, whereas the parent alkaloid inhibits both enzymes. This N-methyl analog therefore could serve to construct a cellular or animal model for Fabry's disease, which is caused by a lack of alpha-galactosidase activity.

Executing and rationalizing the synthesis of a difluorinated analogue of a ring-expanded calystegine B2.[Pubmed:22148579]

J Org Chem. 2012 Jan 20;77(2):991-8.

A difluorinated analogue of a ring-expanded calystegine B(2) and some N-protected species were prepared via microwave-mediated transannular ring-opening of an epoxyketone. The diastereofacial selectivity of the epoxidation reaction, which delivers the key intermediate, and the regioselectivity of the transannular reactions were analyzed by density functional theory (DFT) methods. The epoxidation stereoselectivity arises from simple steric control, whereas the ring-closure reactions are subject to thermodynamic control.

Identification of the glycosidase inhibitors swainsonine and calystegine B2 in Weir vine (Ipomoea sp. Q6 [aff. calobra]) and correlation with toxicity.[Pubmed:7673932]

J Nat Prod. 1995 Jun;58(6):878-86.

The polyhydroxy alkaloid glycosidase inhibitors swainsonine [1] and Calystegine B2 [6] have been identified as constituents of the seeds of the Australian plant Ipomoea sp. Q6 [aff. calobra] (Weir vine) by gas chromatography-mass spectrometry and by their biological activity as inhibitors of specific glycosidases. This plant, which is known only from a small area of southern Queensland, has been reported to produce a neurological disorder when consumed by livestock. The extract of the seeds showed inhibition of alpha-mannosidase, beta-glucosidase, and alpha-galactosidase, consistent with the presence of 1 and alkaloids of the calystegine class. Histological examination of brain tissue from field cases of sheep and cattle poisoned by Weir vine showed lesions similar to those observed in animals poisoned by the swainsonine-containing poison peas (Swainsona spp.) of Australia and locoweeds (Astragalus and Oxytropis spp.) of North America. These results indicate that Weir vine poisoning is an additional manifestation of the induced lysosomal storage disease, mannosidosis, possibly exacerbated by inhibition of the enzymes beta-glucosidase and alpha-galactosidase by Calystegine B2. This is the first reported example of a single plant species capable of producing structurally distinct glycosidase inhibitors, namely, alkaloids of the indolizidine and nortropane classes.

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