Sialic acid containing glycoconjugates are biologically important targets involved in cell-cell recognition, pathogen attack and oncogenesis. The effect of O-protecting groups in sialylations is still a quite unexplored field, when compared to the extensive knowledge acquired in the last decades for monosaccharides such as glucose or galactose. Previously, we reported the effect of Picoloyl at C-4 in the presence of an excess of triflic acid as promoter. Herein we report the synthesis and testing of several mono- and di- picoloylated donors, including a 8-O-picoloyl and a 4,9-O-di picoloyl donors which gave full alpha-only stereoselectivity in all the sialylations tested.

Expansion of the effect of O picoloyl groups in sialylations

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.