Home > Chiral Compounds> Kifunensine,(5R,6R,7S,8R,8aS)-Hexahydro-6,7,8-trihydroxy-5-(hydroxymethyl)-imidazo[1,2-a]pyridine-2,3-dione

Kifunensine,(5R,6R,7S,8R,8aS)-Hexahydro-6,7,8-trihydroxy-5-(hydroxymethyl)-imidazo[1,2-a]pyridine-2,3-dione

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Origin: China

Cas No: 109944-15-2

Specification: 99%min

Min order Quantity: 1 /kg

Supply Ability: 50 mt/month

Lead time: 7 days for OEM, 3 days for ready goods

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CAS No.: 109944-15-2 Formula: C8H12N2O6 Molecular Weight: 232.19100

Description

Kifunensine is an alkaloid originally isolated from Kitasatosporia kifunense, an actinobacterium (formerly called an actinomycete). It is a neutral, stable compound.
Kifunensine is a potent inhibitor of the mannosidase I enzyme and is primarily used in cell culture to make high mannose glycoproteins. Inside a cell, it prevents endoplasmic reticulum mannosidase I (ERM1) from trimming mannose residues from precursor glycoproteins. Kifunensine shows no inhibitory action against mannosidase II or the endoplasmic reticulum alpha-mannosidase, and it weakly inhibits arylmannosidase.
When incorporated in cell culture media, kifunensine has shown no significant impact on cell growth or glycoprotein production yield.
Kifunensine has shown potential for treatment of sarcoglycanopathies and lysosomal storage disorders.

Basic Info

Chemical Name	Kifunensine,(5R,6R,7S,8R,8aS)-Hexahydro-6,7,8-trihydroxy-5-(hydroxymethyl)-imidazo[1,2-a]pyridine-2,3-dione
Synonyms	KIFUNENSINE; KIFUNENSINE,KITASATOSPORIA KIFUNENSE; 1-deoxymannojirimycin;
CAS No.	109944-15-2
Molecular Formula	C8H12N2O6
Molecular Weight	232.19100
PSA	130.33000
LogP	-4.00520

Properties

Melting Point	>280°C

Synthesis Route

Kifunensine diacetonide→Kifunensine,(5R,6R,7S,8R,8aS)-Hexahydro-6,7,8-trihydroxy-5-(hydroxymethyl)-imidazo[1,2-a]pyridine-2,3-dione
2-Deoxy-1,3:4,5-di-O-isopropylidene-2-oxamoylamino-D-mannitol→Kifunensine,(5R,6R,7S,8R,8aS)-Hexahydro-6,7,8-trihydroxy-5-(hydroxymethyl)-imidazo[1,2-a]pyridine-2,3-dione
5-Deoxy-2,3:4,6-di-O-isopropylidene-5-oxamoylamino-D-mannose→Kifunensine,(5R,6R,7S,8R,8aS)-Hexahydro-6,7,8-trihydroxy-5-(hydroxymethyl)-imidazo[1,2-a]pyridine-2,3-dione

Precursor

Kifunensine diacetonide
(2R,3R,4R,5R)-5-amino-2,3:4,6-di(isopropylidenedioxy)hexanol
2-Deoxy-1,3:4,5-di-O-isopropylidene-2-oxamoylamino-D-mannitol
5-Deoxy-2,3:4,6-di-O-isopropylidene-5-oxamoylamino-D-mannose

Downstream Product

Kifunensine diacetonide

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