| Identification | Back Directory | [Name]
KIFUNENSINE | [CAS]
109944-15-2 | [Synonyms]
FR 900494
KIFUNENSINE
Kifunensine min. 99%
[5R-(5α,6β,7α,8α,8aα)]-
KIFUNENSINE, KITASATOSPORIA KIFUNENSE
Hexahydro-6R,7S,8aS-trihydroxy-5R-(hydroxymethyl)-imidazo[1,2-a] pyridine-2,3-dione
(5R,6R,7S,8R,8AS)-6,7,8-trihydroxy-5-(hydroxymethyl)hexahydroimidazo[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
Imidazo1,2-apyridine-2,3-dione, hexahydro-6,7,8-trihydroxy-5-(hydroxymethyl)-, (5R,6R,7S,8R,8aS)-
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 | [Molecular Formula]
C8H12N2O6 | [MDL Number]
MFCD00270017 | [MOL File]
109944-15-2.mol | [Molecular Weight]
232.19 |
| Chemical Properties | Back Directory | [Appearance]
White Powder | [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 | [Water Solubility ]
Soluble to 5 mM in water with sonication | [Stability:]
Desiccate and Store at -20°C |
| Hazard Information | Back Directory | [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 | [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. | [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 | [General Description]
A potent alkaloid inhibitor of mannosidase I. Does not affect mannosidase II and the endoplasmic reticulum α-mannosidase. | [Biochem/physiol Actions]
Product does not compete with ATP. | [storage]
Store at -20°C | [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 |
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