C-linked glycosides, as compared to O-linkages, have been a target of study for the catabolic stability imparted by removal of the acetal functionality. Lacking an anomeric effect, the control of the resulting chair conformation and positioning of the C-linkage have been dependent on steric forces alone. In our program to develop robust mimics of Tn antigen (<i>O</i>-GalNAc-α-Ser/Thr), we are developing approaches to introduce a pendant hydroxyl off the C-linkage to alter conformational preferences through possible intramolecular H-bonding. Two stages of our early synthetic work: installation of the pendant hydroxyl and construction of the full carbon skeleton will be presented.

Design of and synthetic progress toward a novel C-linked GalNAc-α-serine

251st National Meeting (2016)

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