Synthetic tools for the characterization of galactofuranosyl transferases: glycosylations via acylated glycosyl iodides

With the aim of developing synthetic tools for the characterization of galactofuranosyltransferases, the synthesis of 9-decenyl glycosides of D-Manp, D-Galf, and beta-D-Galf-(1 -> 3)-D-Manp was targeted. The interest in the alkenyl aglycone arises via potential conjugation reactions, once the terminal double bond has been conveniently functionalized. The glycosylation of beta-D-Galf-(1 -> 3)-D-Manp was attempted by two different approaches: the trichloroacetimidate method and the glycosylation via the glycosyl iodide. The conditions for the latter were established on the basis of glycosylation assays of per-O-acetylmannose. On the other hand, the study of glycosylation reactions via per-O-benzoylated galactofuranosyl iodide confirms the versatility of glycosyl iodides as donors. (C) 2013 Elsevier Ltd. All rights reserved.