A new class of glycosidase inhibitor: synthesis of salacinol and its stereoisomers.
Salacinol (4) is one of the active principles in the aqueous extracts of Salacia reticulata that are traditionally used in Sri Lanka and India for the treatment of diabetes. The syntheses of salacinol (4), the enantiomer of salacinol (5), and a diastereomer (7) are described. The synthetic strategy relies on the selective nucleophilic attack of 2,3,5-tri-O-benzyl-1,4-anhydro-4-thio-D- or L-arabinitol at C-1 of 2,4-O-benzylidene D- or L-erythritol-1,3-cyclic sulfate. The work serves to resolve the ambiguity about the exact structure of salacinol and establishes conclusively the structure of the natural product.
Ghavami
A
A
Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, Canada V5A 1S6.
Johnston
B D
BD
Pinto
B M
BM
D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D008968:Molecular Conformation; D010936:Plant Extracts / Q000138:chemical synthesis / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013402:Sugar Alcohols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013431:Sulfates; D013452:Sulfonium Compounds / Q000138:chemical synthesis / Q000737:chemistry
D004791:Enzyme Inhibitors; D010936:Plant Extracts; D013402:Sugar Alcohols; D013431:Sulfates; D013452:Sulfonium Compounds; C427963:salacinol; D006026:Glycoside Hydrolases