Castanospermine-trehazolin hybrids: a new family of glycomimetics with tuneable glycosidase inhibitory properties.
Bicyclic azasugar glycomimetics related to castanospermine and trehazolin have been prepared from sugar carbodiimides via aminooxazoline intermediates; preliminary enzyme inhibition tests showed a marked dependence of the selectivity and potency towards alpha and beta-glucosidases upon the nature of the exocyclic substituent.
García-Moreno
M Isabel
MI
Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, Apartado 553, E-41071 Sevilla, Spain.
Díaz-Pérez
Paula
P
Ortiz Mellet
Carmen
C
García Fernández
José M
JM
D001667:Binding, Competitive; D004187:Disaccharides / Q000138:chemical synthesis*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D065089:Glycoside Hydrolase Inhibitors; D006863:Hydrogen-Ion Concentration; D007212:Indolizines / Q000138:chemical synthesis*; D015394:Molecular Structure; D010944:Plants / Q000201:enzymology; D014198:Trehalase / Q000037:antagonists & inhibitors; D001617:beta-Glucosidase / Q000037:antagonists & inhibitors*; D054836:Indolizidines
D004187:Disaccharides; D004791:Enzyme Inhibitors; D065089:Glycoside Hydrolase Inhibitors; D007212:Indolizines; D014198:Trehalase; D001617:beta-Glucosidase; C071816:trehazolin; C037806:castanospermine; D054836:Indolizidines