A New Class of Glycosidase Inhibitor: Synthesis of Salacinol and Its Stereoisomers
| Autor: | Ahmad Ghavami, B. M. Pinto, Blair D. Johnston |
|---|---|
| Rok vydání: | 2001 |
| Předmět: |
Salacia reticulata
Natural product Glycoside Hydrolases biology Plant Extracts Sulfates Chemistry Stereochemistry Organic Chemistry Molecular Conformation Sulfonium Compounds Diastereomer Glycosidase inhibitor Stereoisomerism biology.organism_classification Structure-Activity Relationship chemistry.chemical_compound Sugar Alcohols Organic chemistry Structure–activity relationship Enzyme Inhibitors Sri lanka Enantiomer |
| Zdroj: | The Journal of Organic Chemistry. 66:2312-2317 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo001444g |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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