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

BALDONI L.; MARINO C.

CARBOHYDRATE RESEARCH

ELSEVIER SCI LTD

Lugar: Amsterdam; Año: 2012

0008-6215

With the aim to develop synthetic tools for the characterization of galactofuranosyltransferases, the synthesis of 9-decenyl glycosides of D-Manp, D-Galf and b-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 b-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-bezoylated galactofuranosyl iodide confirms the versatility of glycosyl iodides as donors.