(5R,6R,7S,8R,8aS)-6,7,8-Trihydroxy-5-(hydroxymethyl)hexahydroimidazo[1,2-a]pyridine-2,3-dione - CAS 109944-15-2

Catalog: BB002564
Product Name: (5R,6R,7S,8R,8aS)-6,7,8-Trihydroxy-5-(hydroxymethyl)hexahydroimidazo[1,2-a]pyridine-2,3-dione
CAS: 109944-15-2
Synonyms: [5R-(5α,6β,7α,8α,8aα)]-Hexahydro-6,7,8-trihydroxy-5-(hydroxymethyl)-imidazo[1,2-a]pyridine-2,3-dione; (+)-Kifunensine; FR 900494; (5R,6R,7S,8R,8aS)-6,7,8-trihydroxy-5-(hydroxymethyl)hexahydroimidazo[1,2-a]pyridine-2,3-dione; Imidazo(1,2-a)pyridine-2,3-dione, hexahydro-6,7,8-trihydroxy-5-(hydroxymethyl)-, (5R-(5alpha,6beta,7alpha,8alpha,8aalpha))-
IUPAC Name:(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
Description:(5R,6R,7S,8R,8aS)-6,7,8-Trihydroxy-5-(hydroxymethyl)hexahydroimidazo[1,2-a]pyridine-2,3-dione (CAS# 109944-15-2) 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.
Molecular Weight:232.19
Molecular Formula:C8H12N2O6
Canonical SMILES:C(C1C(C(C(C2N1C(=O)C(=O)N2)O)O)O)O
Melting Point:>208°C (dec.)
Density:1.85±0.1 g/cm3 (Predicted)
Solubility:Soluble in DMSO (Slightly, Heated), Methanol (Very Slightly, Heated, Sonicated), Water (Very Slightly)
Appearance:White to Off-white Solid
Storage:Store at -20°C

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