Synthesis of 1,5-dideoxy-3-O-(α-D-mannopyranosyl)-1,5-imino-D-mannitol and 1,5-dideoxy-3-O-(α-D-glucopyranosyl)-1,5-imino-D-mannitol: Powerful inhibitors of endomannosidase

Helen Ardron,Terry D Butters,Frances M Platt,Mark R Wormald,Raymond A Dwek,George W.J Fleet,Gary S Jacob

doi:10.1016/s0957-4166(00)82250-8

Synthesis of 1,5-dideoxy-3-O-(α-D-mannopyranosyl)-1,5-imino-D-mannitol and 1,5-dideoxy-3-O-(α-D-glucopyranosyl)-1,5-imino-D-mannitol: Powerful inhibitors of endomannosidase

Helen Ardron, Terry D Butters + Show 5 more

https://doi.org/10.1016/s0957-4166(00)82250-8

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Journal: Tetrahedron: Asymmetry	Publication Date: Jan 1, 1993
Citations: 21

Affiliation: University of Oxford, Monsanto (United States)

#Potential Use #Pathways Of Processing + Show 5 more

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Abstract

The synthesis and conformations of 3-O-methylDMJ, 3-O-(α-D-glucopyranosyl)-DMJ (Glcα1,3DMJ), and 3-O-(α-D-mannopyranosyl)-DMJ (Manα1,3DMJ) are described. Manα1,3DMJ and Glcα1,3DMJ are shown to be very powerful inhibitors of an endomannosidase. The potential use of these compounds in both probing the pathways of N-linked glycoprotein processing and in the chemotherapy of some viral diseases is discussed.

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