Protein glycosylation of serine/threonine residues is of biological importance in both cellular recognition and cellular signaling.  �-GlcNAc glycoconjugates have been linked to cellular signaling in diabetes and neurodegenerative diseases, while a-GalNAc is the core carbohydrate found in mucins and is a tumor-associated cell surface carbohydrate antigen.  The natural oxygen-linkage is susceptible to biological factors including hydrolysis and enzymatic cleavage, so the methylene substituted isosteres provide more robust targets.  Previously, we have reported the pathways to both a- and �-isomers of 1  by an olefin metathesis/hydroalkoxylation strategy.  We now report the synthesis of the a-linked C-GalNAc serine 2   and efforts towards incorporation of the C-2 acetamido functionality to provide C-linked (�)-GlcNAc and (a)-GalNAc   serines 3  and 4  .

Synthesis of C-linked (β)-Glc and (α)-Gal serines and efforts toward incorporation of the C-2 acetamido functionality

244th National Meeting (2012)

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