Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2010, Issue 29, Pages 5574-5585Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201000632
Keywords
Azasugars; Enzymes; Inhibitors; Molecular modeling; Biological activity
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Funding
- Minister dell'Istruzione, dell'Universitia e della Ricerca
- Ente Cassa di Risparmio di Firenze, Italy
- Consorzio Interuniversitario Nazionale Metodologie e Processi Innovativi di Sintesi
- Swiss National Science Foundation
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We report the total synthesis of a series of pyrrolizidine analogues of casuarine (1) and their 6-O-alpha-glucoside derivatives. The synthetic strategy is based on a totally regio- and stereoselective 1,3-dipolar cycloaddition of suitably substituted alkenes and a carbohydrate-based nitrone. We also report the evaluation of the biological activity of casuarine and its derivatives towards a wide range of glycosidases and a molecular modeling study focused on glucoamylase (GA) in which the binding modes of the newly synthesized compounds within the enzyme cavity are investigated. The results highlight the prominent structural features of casuarine and its derivatives that make them selective glucoamylase inhibitors.
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