Looking glass inhibitors: efficient synthesis and biological evaluation of D-deoxyfuconojirimycin

Yves Blériot; Dirk Gretzke; Thomas M Krülle; Terry D Butters; Raymond A Dwek; Robert J Nash; Naoki Asano; George W J Fleet

doi:10.1016/j.carres.2005.10.002

Looking glass inhibitors: efficient synthesis and biological evaluation of D-deoxyfuconojirimycin

Carbohydr Res. 2005 Dec 30;340(18):2713-8. doi: 10.1016/j.carres.2005.10.002. Epub 2005 Nov 4.

Authors

Yves Blériot¹, Dirk Gretzke, Thomas M Krülle, Terry D Butters, Raymond A Dwek, Robert J Nash, Naoki Asano, George W J Fleet

Affiliation

¹ Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK. yves.bleriot@chimie.ens.fr

PMID: 16274755
DOI: 10.1016/j.carres.2005.10.002

Abstract

1,6-Dideoxygalactostatin, the mirror image of 1-deoxy-L-fuconojirimycin, was efficiently prepared from 2,3-O-isopropylidene-L-lyxonolactone in four steps and evaluated as a glycosidase inhibitor.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

1-Deoxynojirimycin / analogs & derivatives
Glycoside Hydrolases / antagonists & inhibitors*
Humans
Imino Pyranoses / chemical synthesis
Imino Pyranoses / chemistry
Imino Pyranoses / pharmacology
Molecular Conformation
Stereoisomerism
Structure-Activity Relationship
Sugar Alcohols / chemical synthesis*
Sugar Alcohols / chemistry
Sugar Alcohols / pharmacology*

Substances

Imino Pyranoses
Sugar Alcohols
1-Deoxynojirimycin
deoxyfuconojirimycin
Glycoside Hydrolases