Abstract
Four series of analogues of the naturally occurring glucosidase inhibitor salacinol were synthesized for structure–activity studies with different glycosidase enzymes. The target zwitterionic compounds were synthesized by means of nucleophilic attack at the least-hindered carbon atom of the 1,3-cyclic sulfates derived from D-glucose and D-mannose by the isopropylidene-protected 1,4-anhydro-4-thio- and seleno-D-allitols and the 4-thio- and seleno-L-allitols. Deprotection of the coupled products afforded the novel sulfonium and selenonium ions containing polyhy droxylated acyclic chains of four and six carbons, with different stereochemistry at the stereogenic centers and with 1,4-anhydro-4-seleno or 4-thio-D- or L- alditol heterocyclic rings. The compounds showed no significant activity against recombinant human maltase glucoamylase (MGA), a critical intestinal glucosidase involved in the processing of oligosaccharides of glucose into glucose itself.Key words: glycosidase inhibitors, zwitterionic, selenonium salts, sulfonium salts, cyclic sulfates, L-ascorbic acid, D-gulonic-γ-lactone.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
8 articles.
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