ChemicalBook > CAS DataBase List > KIFUNENSINE

KIFUNENSINE

Product Name: KIFUNENSINE
CAS No.: 109944-15-2
Chemical Name: KIFUNENSINE
Synonyms: FR 900494;Kifunensin;KIFUNENSINE;Kifunensine min. 99%;Kifunensine - Bio-X ?;[5R-(5α,6β,7α,8α,8aα)]-;Kifunensine, (+)- - FR 900494;KIFUNENSINE, KITASATOSPORIA KIFUNENSE;Kifunensine, Kitasatosporia kifunense;Kifunensine, class I alpha-mannosidase inhibitor
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
biological source: synthetic (organic)
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: $285
Updated: 2025/07/31

Sigma-Aldrich

Product number: 422500
Product name: Kifunensine
Purity: A potent alkaloid inhibitor of mannosidase I.
Packaging: 1mg
Price: $401
Updated: 2025/07/31

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] 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

Raw materials

Preparation Products

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109944-15-2, KIFUNENSINERelated Search:

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

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

Kifunensine, class I alpha-mannosidase inhibitor

Kifunensine, <i>Kitasatosporia kifunense</i>

Kifunensine - Bio-X ?

109944-15-2

C8H12N2O6

Antibiotics

All Inhibitors

Glycosidase Inhibitors

Inhibitors