Synthetic tools for the characterization of galactofuranosyl transferases. Glycosylations via acylated glycosyl iodides

Abstract

With the aim to develop 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 from its 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-Oacetylmannose.On the other hand, the study of glycosylation reactions via per-O-bezoylated galactofuranosyl iodide confirms the versatility of glycosyl iodides as donors.