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

Water Solubility 

Soluble to 5 mM in water with sonication

Stability:

Desiccate and Store at -20°C

Safety Information

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 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)?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(109944-15-2)Related Product Information

• VERATRIDINE
• Mupirocin
• 2-AMINOPIPERIDINE
• N,N'-Bis(2-hydroxyethyl)oxamide
• (R)-3-ISOPROPYLAMINO-1,2-PROPANEDIOL
• 1-ACETYLPIPERIDIN-4-OL
• 2-AMINO-1-PIPERIDIN-1-YL-ETHANONE HCL
• 2-(2-methylpiperidin-1-yl)ethanamine
• N-(2-AMINOETHYL)-4-PIPERIDINOL
• CHEMBRDG-BB 4011096
• 4-HYDROXY-PIPERIDINE-1-CARBALDEHYDE
• KIFUNENSINE DIACETONIDE
• DEOXYMANNOJIRIMYCIN
• 1-(2-AMINO-ETHYL)-PIPERIDIN-3-OL
• KIFUNENSINE
• 8-epi-Kifunensine
• 8a-epi-Kifunensine
• Kifunensine pentaacetate