Looking glass inhibitors: efficient synthesis and biological evaluation of D-deoxyfuconojirimycin.
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.
Blériot
Yves
Y
Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK. yves.bleriot@chimie.ens.fr
Gretzke
Dirk
D
Krülle
Thomas M
TM
Butters
Terry D
TD
Dwek
Raymond A
RA
Nash
Robert J
RJ
Asano
Naoki
N
Fleet
George W J
GW
D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D006801:Humans; D050112:Imino Pyranoses / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D008968:Molecular Conformation; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013402:Sugar Alcohols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D050112:Imino Pyranoses; D013402:Sugar Alcohols; D017485:1-Deoxynojirimycin; C062662:deoxyfuconojirimycin; D006026:Glycoside Hydrolases