Synthesis of 5′-seleno-xylofuranosides

The synthesis of selenium derivatives of naturally occurring chiral molecules is becoming increasingly important in recent years. In this context, we describe herein an easy, straightforward synthetic route for the preparation of a series of chiral seleno-furanosides, starting from the readily available carbohydrate D-xylose. In addition, selected compounds were screened as inhibitors of the delta-aminolevulinate dehyclratase (delta-ALA-D) enzyme. Diselenide 4 was found to reduce significantly the enzymatic activity, while seleno-furanoside la increased delta-ALA-D activity. (C) 2010 Elsevier Ltd. All rights reserved.