Synthesis of densely functionalized enantiopure indolizidines by ring- closing metathesis (RCM) of hydroxylamines from carbohydrate- derived nitrones

• Marco Bonanni,
• Marco Marradi,
• Francesca Cardona,
• Stefano Cicchi and
• Andrea Goti

Beilstein J. Org. Chem. 2007, 3, No. 44, doi:10.1186/1860-5397-3-44

• instance, the plant-derived polyhydroxylated indolizidines are well known as potent glycosidases inhibitors, and for this reason they are potential therapeutic agents. [2][3][4] A great deal of research is still devoted to the structural elucidation of these alkaloids as well as to their total syntheses

Synthesis and glycosidase inhibitory activity of new hexa- substituted C8-glycomimetics

• Olivia Andriuzzi,
• Christine Gravier-Pelletier,
• Gildas Bertho,
• Thierry Prangé and
• Yves Le Merrer

Beilstein J. Org. Chem. 2005, 1, No. 12, doi:10.1186/1860-5397-1-12

• , Laboratoire de Cristallographie et RMN Biologiques, 4 avenue de l'Observatoire, 75270 Paris Cedex 06, France 10.1186/1860-5397-1-12 Abstract Background Glycosidases are involved in several metabolic pathways and the development of inhibitors is an important challenge towards the treatment of diseases, such

• particular case, due to the hindered conformation of such epoxides as demonstrated by X-ray cristallographic analysis. Conclusion The biological activity of the synthesized glycomimetics has been evaluated towards 24 commercially available glycosidases. The weak observed activities can probably be related to

• towards glycosidases, while the core structure and essential network of hydroxyl functionalities for enzyme recognition are retained. An important example is the 1-deoxynojirimycin (DNJ) family, for which DNJ itself is a competitive inhibitor of α-D-glucosidase (Ki = 8–25 μM),[10] while its derivatives

Methods for the synthesis of polyhydroxylated piperidines by diastereoselective dihydroxylation: Exploitation in the two-directional synthesis of aza-C-linked disaccharide derivatives

• Andrew Kennedy,
• Adam Nelson and
• Alexis Perry

Beilstein J. Org. Chem. 2005, 1, No. 2, doi:10.1186/1860-5397-1-2

• LS2 9JT, UK School of Chemistry, University of Leeds, Leeds LS2 9JT, UK 10.1186/1860-5397-1-2 Abstract Background Many polyhydroxylated piperidines are inhibitors of the oligosaccharide processing enzymes, glycosidases and glycosyltransferases. Aza-C-linked disaccharide mimetics are compounds in

• polyhydroxylated piperidines are potent inhibitors of the oligosaccharide processing enzymes, glycosidases and glycosyltransferases.[1][2][3] For example, deoxymannojirimycin, 1, and deoxynojirimycin, 2, are selective mannosidase and glucosidase inhibitors respectively.[4][5] In these molecules, the nitrogen atom