Total asymmetric synthesis of (−)-conduramine B-1 and of its enantiomer. N-Benzyl derivatives of conduramine B-1 are β-glucosidase inhibitors
| Autor: | Catherine Schütz, Robert Łysek, Pierre Vogel |
|---|---|
| Rok vydání: | 2005 |
| Předmět: |
Stereochemistry
Clinical Biochemistry Pharmaceutical Science Stereoisomerism Saccharomyces cerevisiae Biochemistry Bacteria Anaerobic Bridged Bicyclo Compounds Structure-Activity Relationship Non-competitive inhibition Cyclohexenes Drug Discovery Cellulases Glycoside Hydrolase Inhibitors Enzyme Inhibitors Molecular Biology chemistry.chemical_classification Molecular Structure biology Organic Chemistry Enantioselective synthesis Absolute configuration Total synthesis Hexosamines Xylosidases Enzyme chemistry Enzyme inhibitor biology.protein Molecular Medicine Aspergillus niger Prunus Enantiomer |
| Zdroj: | Bioorganic & Medicinal Chemistry Letters. 15:3071-3075 |
| ISSN: | 0960-894X |
| Popis: | The 'naked sugars' (+)- and (-)-7-oxabicyclo[2.2.1]hept-5-en-2-one have been converted into (-)-conduramine B-1 ((-)-3) and its enantiomer (+)-3, respectively. They have been condensed with a variety of aldehydes in the presence of NaBH(OAc)(3). The N-substituted derivatives 4 and ent-4 so-obtained have been tested against two alpha-glucosidases, two amyloglucosidases, two beta-glucosidases and one beta-xylosidase for their inhibitory activities. Although (-)-3 and (+)-3 do not inhibit any of these enzymes at 1mM concentration, N-benzylated derivatives of (-)-conduramine B-1 are selective and competitive inhibitors of beta-glucosidases with K(i) in low micromolecular range. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full Text from ScienceDirect