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
- Molecular Weight:
- 232.19
- MDL Number:
- MFCD00270017
- MOL File:
- 109944-15-2.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| 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 |
| FDA UNII | 0NI8960271 |
| UNSPSC Code | 12352204 |
| NACRES | NA.77 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H319 | |||||||||
| Precautionary statements | P264-P280-P305+P351+P338-P337+P313 | |||||||||
| WGK Germany | 3 | |||||||||
| HS Code | 2939800000 | |||||||||
| Storage Class | 11 - Combustible Solids | |||||||||
| Hazard Classifications | Eye Irrit. 2 | |||||||||
| NFPA 704 |
|
KIFUNENSINE price More Price(51)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | K1140 | Kifunensine mannosidase inhibitor | 109944-15-2 | 1mg | $305 | 2026-04-30 | Buy |
| Sigma-Aldrich | 422500 | Kifunensine A potent alkaloid inhibitor of mannosidase I. | 109944-15-2 | 1mg | $430 | 2026-04-30 | Buy |
| Cayman Chemical | 10009437 | Kifunensine ≥98% | 109944-15-2 | 1mg | $74 | 2026-04-30 | Buy |
| Cayman Chemical | 10009437 | Kifunensine ≥98% | 109944-15-2 | 5mg | $203 | 2026-04-30 | Buy |
| Cayman Chemical | 10009437 | Kifunensine ≥98% | 109944-15-2 | 10mg | $295 | 2026-04-30 | Buy |
KIFUNENSINE Chemical Properties, Uses, Production
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
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Dingyuan (Tianjin) Biomedical Technology Co., LTD | 15522139451 | dingy_2018@163.com | China | 12 | 58 |
| J & K SCIENTIFIC LTD. | 18210857532 18210857532 | jkinfo@jkchemical.com | China | 96815 | 76 |
| 3B Pharmachem (Wuhan) International Co.,Ltd. | 18930552037 | 3bsc@sina.com | China | 15813 | 69 |
| Chemsky（shanghai）International Co.,Ltd. | 021-50135380 | shchemsky@sina.com | China | 32273 | 50 |
| Shanghai T&W Pharmaceutical Co., Ltd. | +86 21 61551611 | China | 9874 | 58 | |
| Shanghai Aladdin Bio-Chem Technology Co.,LTD | 400-6206333 13167063860 | anhua.mao@aladdin-e.com | China | 29977 | 65 |
| SHANGHAI FORTUNE CHEMICAL TECHNOLOGY CO., LTD | 13816107857 | sales@fortunechem-sh.com | China | 981 | 58 |
| ShangHai Caerulum Pharma Discovery Co., Ltd. | 18149758185 18149758185 | sales-cpd@caerulumpharma.com | China | 3493 | 58 |
| Shanghai Macklin Biochemical Co.,Ltd. | 15221275939 15221275939 | shenlinxing@macklin.cn | China | 15775 | 55 |
| Sigma-Aldrich | 021-61415566 800-8193336 | orderCN@merckgroup.com | China | 51389 | 80 |
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