|
|
| | 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 | | biological source | synthetic (organic) | | Water Solubility | Soluble to 5 mM in water with sonication | | Stability: | Desiccate and Store at -20°C | | InChI | 1S/C8H12N2O6/c11-1-2-3(12)4(13)5(14)6-9-7(15)8(16)10(2)6/h2-6,11-14H,1H2,(H,9,15)/t2-,3-,4+,5+,6+/m1/s1 | | InChIKey | OIURYJWYVIAOCW-PQMKYFCFSA-N | | SMILES | N21[C@H](NC(=O)C2=O)[C@H]([C@H]([C@@H]([C@H]1CO)O)O)O |
| WGK Germany | 3 | | HS Code | 2939800000 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2 |
| | KIFUNENSINE Usage And Synthesis |
| Description | Historically isolated from Kitasatosporia kifunense.1Kifunensine (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 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. | | storage | Store at -20°C | | References | [1] M IWAMI. A new immunomodulator, FR-900494: taxonomy, fermentation, isolation, and physico-chemical and biological characteristics.[J]. Journal of Antibiotics, 1987, 40 5: 612-622. DOI:10.7164/antibiotics.40.612
[2] A D ELBEIN. Kifunensine, a potent inhibitor of the glycoprotein processing mannosidase I.[J]. The Journal of Biological Chemistry, 1990, 265 26: 15599-15605.
[3] MARC BARTOLI. Mannosidase I inhibition rescues the human alpha-sarcoglycan R77C recurrent mutation.[J]. Human molecular genetics, 2008, 17 9: 1214-1221. DOI:10.1093/hmg/ddn029
[4] FAN WANG. Inhibition of endoplasmic reticulum-associated degradation rescues native folding in loss of function protein misfolding diseases.[J]. The Journal of Biological Chemistry, 2011: 43454-43464. DOI:10.1074/jbc.m111.274332 |
| | KIFUNENSINE Preparation Products And Raw materials |
|