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

• 9-Decenyl glycosides of d-Manp, d-Galf, and β-d-Galf-(1→3)-d-Manp were synthesized.
• Conditions for glycosylation of per-O-acetyl-Manp iodide were revised and optimized.
• The established conditions were used for the glycosylation of β-d-Galf-(1→3)-d-Manp.
• Galactofuranosylation via per-O-benzoyl-β-d-Galf iodide was investigated.

With the aim of developing synthetic tools for the characterization of galactofuranosyltransferases, the synthesis of 9-decenyl glycosides of d-Manp, d-Galf, and β-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 β-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.

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