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KIFUNENSINE

Product Name
KIFUNENSINE
CAS No.
109944-15-2
Chemical Name
KIFUNENSINE
Synonyms
FR 900494;Kifunensin;KIFUNENSINE;Kifunensine min. 99%;[5R-(5α,6β,7α,8α,8aα)]-;Kifunensine, (+)- - FR 900494;KIFUNENSINE, KITASATOSPORIA KIFUNENSE;Kifunensine, Kitasatosporia kifunense - CAS 109944-15-2 - Calbiochem;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
CBNumber
CB7233173
Molecular Formula
C8H12N2O6
Formula Weight
232.19
MOL File
109944-15-2.mol
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KIFUNENSINE Property

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
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Safety

WGK Germany 
3
HS Code 
2939800000
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P337+P313IF eye irritation persists: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
K1140
Product name
Kifunensine
Purity
mannosidase inhibitor
Packaging
1mg
Price
$263
Updated
2024/03/01
Sigma-Aldrich
Product number
422500
Product name
Kifunensine
Purity
A potent alkaloid inhibitor of mannosidase I.
Packaging
1mg
Price
$390
Updated
2024/03/01
Cayman Chemical
Product number
10009437
Product name
Kifunensine
Purity
≥98%
Packaging
1mg
Price
$65
Updated
2024/03/01
Cayman Chemical
Product number
10009437
Product name
Kifunensine
Purity
≥98%
Packaging
5mg
Price
$179
Updated
2024/03/01
Cayman Chemical
Product number
10009437
Product name
Kifunensine
Purity
≥98%
Packaging
10mg
Price
$260
Updated
2024/03/01
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KIFUNENSINE Chemical Properties,Usage,Production

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 Preparation Products And Raw materials

Raw materials

Preparation Products

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109944-15-2, KIFUNENSINERelated Search:


  • 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
  • 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
  • KIFUNENSINE
  • KIFUNENSINE, KITASATOSPORIA KIFUNENSE
  • Imidazo1,2-apyridine-2,3-dione, hexahydro-6,7,8-trihydroxy-5-(hydroxymethyl)-, (5R,6R,7S,8R,8aS)-
  • Kifunensin
  • 109944-15-2
  • C8H12N2O6
  • Antibiotics
  • All Inhibitors
  • Glycosidase Inhibitors
  • Inhibitors