Synthesis, Conformational Analysis, and Evaluation as Glycosidase Inhibitors of Two Ether-Bridged Iminosugars.
- Resource Type
- Article
- Authors
- Luo, Bo; Marcelo, Filipa; Désiré, Jérôme; Zhang, Yongmin; Sollogoub, Matthieu; Kato, Atsushi; Adachi, Isao; Cañada, F.Javier; Jiménez-Barbero, Jesús; Blériot, Yves
- Source
- Journal of Carbohydrate Chemistry. Sep-Dec2011, Vol. 30 Issue 7-9, p641-654. 14p.
- Subject
- *CONFORMATIONAL analysis
*GLYCOSIDASE inhibitors
*IMINOSUGARS
*POLYPHENOLS
*ISOMERIZATION
*MOLECULAR models
*GLUCOSIDASES
*RING formation (Chemistry)
- Language
- ISSN
- 0732-8303
Two bicyclic iminosugars have been synthesized from polyhydroxylated azepanes by ring isomerization followed by debenzylative cyclization. Their conformations have been studied by NMR and molecular modeling and their glycosidase inhibition profiles were determined. They both adopt a chair conformation for the piperidine ring and display weak inhibition on α-glucosidases. [ABSTRACT FROM PUBLISHER]