Kifunensine

CAS: 109944-15-2

Ref. TR-K450000

Product Information

• Name: Kifunensine
• Synonyms: (5R,6R,7S,8R,8aS)-6,7,8-trihydroxy-5-(hydroxymethyl)-1,5,6,7,8,8a-hexahydroimidazo[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, Fr 900494, Imidazo[1,2-a]pyridine-2,3-dione, hexahydro-6,7,8-trihydroxy-5-(hydroxymethyl)-, (5R,6R,7S,8R,8aS)-, Imidazo[1,2-a]pyridine-2,3-dione, hexahydro-6,7,8-trihydroxy-5-(hydroxymethyl)-, [5R-(5α,6β,7α,8α,8aα)]-

Description

Stability Desiccate and Store at -20°C
Applications 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
References Iwami, M., et al.: J. Antibiotic., 40, 612 (1987); Elbein, A.D., et al.: J. Biol. Chem., 265, 15599 (1990); Elbein, A.D., et al.: Archives of Biochem & Biophys., 288, 1, 177 (1991); Kayakiri, H., et al.: Chem. Pharm. Bull., 39(6), 1378 (1991)

• Brand: TRC

Chemical properties

• Molecular weight: 232.19
• Formula: C₈H₁₂N₂O₆
• Color/Form: White To Off-White
• InChI: 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
• InChI key: InChIKey=OIURYJWYVIAOCW-PQMKYFCFSA-N
• SMILES: O=C1N[C@@H]2[C@@H](O)[C@@H](O)[C@H](O)[C@@H](CO)N2C1=O