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| KIFUNENSINE Basic information |
| Product Name: | KIFUNENSINE | | Synonyms: | Kifunensine, Kitasatosporia kifunense - CAS 109944-15-2 - Calbiochem;Kifunensine, (+)- - FR 900494;FR 900494, Hexahydro-6R,7S,8aS-trihydroxy-5R-(hydroxymethyl)-imidazo[1,2-a] pyridine-2,3-dione;(5R,8aS)-1,5,6,7,8,8a-Hexahydro-6β,7α,8α-trihydroxy-5α-(hydroxymethyl)imidazo[1,2-a]pyridine-2,3-dione;(5R,6R,7S,8R,8aS)-Hexahydro-6,7,8-trihydroxy-5-(hydroxymethyl)-imidazo[1,2-a]pyridine-2,3-dione;[5R-(5α,6β,7α,8α,8aα)]-;Kifunensine min. 99%;FR 900494 | | CAS: | 109944-15-2 | | MF: | C8H12N2O6 | | MW: | 232.19 | | EINECS: | | Product Categories: | Antibiotics;All Inhibitors;Glycosidase Inhibitors;Inhibitors | | Mol File: | 109944-15-2.mol |
| KIFUNENSINE Chemical Properties |
| Melting point | >280°C | | density | 1.85±0.1 g/cm3(Predicted) | | storage temp. | −20°C | | solubility | water, double-distilled: soluble50MM | | form | White solid | | pka | 9.61±0.70(Predicted) | | color | White | | Stability: | Desiccate and Store at -20°C |
| WGK Germany | 3 | | HS Code | 2939800000 |
| KIFUNENSINE Usage And Synthesis |
| Description | Historically isolated from Kitasatosporia kifunense.1?Kifunensine (CAS 109944-15-2) is an inhibitor of class I α-mannosidases which inhibit glycoprotein processing. Inhibits human endoplasmic reticulum α-1,2-mannosidase I and Golgi Class I mannosidases IA, IB and IC with Ki values of 130 and 23 nM respectively.2 Inhibition of endoplasmic reticulum a-mannosidase I activity rescues the human a-sarcoglycan R77C mutation suggesting a new pharmacological approach for limb girdle muscular dystrophy type 2D patients carrying mutations that impair a-sarcoglycan trafficking.3 Improves maturation of misfolded proteins.4 | | Chemical Properties | White Powder | | Uses | Kifunensine is an alkaloid produced by the fungus, Kitasatosporia kifunense, and has been shown to be a weak inhibitor of aryl mannosidase. It is a unique oxamide derivative of mannojirimycin and a potent inhibitor of the glycoprotein processing enzyme | | Uses | Kifunensine is an alkaloid produced by the fungus, Kitasatosporia kifunense, and has been shown to be a weak inhibitor of aryl mannosidase. It is a unique oxamide derivative of mannojirimycin and a potent inhibitor of the glycoprotein processing enzyme mannosidase I. Kifunenesine is ineffective in inhibiting either mannosidase II or the endoplasmic reticulum (ER) a-mannosidase. It also possesses immunomodulating properties based on chemical, physicochemical and x-ray crystallographic analysis.When tested in cell culture using influenza virus-infected MDCK cells, kifunensine, at 1 mg/ml or less, caused almost complete inhibition of complex chain formation with the accumulation of Man9(GlcNAc)2. Thus, kifunensine was proven to be 50 to 100 times more effective than deoxymannojirimycin.Ph | | General Description | A potent alkaloid inhibitor of mannosidase I. Does not affect mannosidase II and the endoplasmic reticulum α-mannosidase. | | Biological Activity | Inhibitor of class I α -mannosidases that inhibits glycoprotein processing. Inhibits human endoplasmic reticulum α -1,2-mannosidase I and Golgi Class I mannosidases IA, IB and IC with K i values of 130 and 23 nM respectively. | | Biochem/physiol Actions | Product does not compete with ATP. | | References | 1)?Iwami et al. (1987), A new immunomodulator, FR-900494: taxonomy, fermentation, isolation, and physico-chemical and biological characteristics; J.Antibiot. (Tokyo) 40 612
2)?Elbein et al. (1990), Kifunensine, a potent inhibitor of the glycoprotein processing mannosidase I; ?J.Biol.Chem. 265 15599
3)?Bartoli et al. (2008), Mannosidase I inhibition rescues the human alpha-sarcoglycan R77C recurrent mutation; ?Hum.Mol.Genet. 17 1214
4)?Wang et al. (2011), Inhibition of endoplasmic reticulum-associated degradation rescues native folding in loss of function protein misfolding diseases; J.Biol.Chem. 286 43454 |
| KIFUNENSINE Preparation Products And Raw materials |
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