In mammalian cells, glycans containing sialic acid play a significant role in many biologically relevant processes such as influenza virus infection. In order to adapt to environmental changes, sialic acid adopts variations at the hydroxyl groups, the most common form being the O-acetyl groups.  Isolation of partially O-acetylated sialic acid is challenging due to harsh conditions used in extraction methods; thus, syntheses of these analogues are important.  Six partially O-acetylated N-acetyl neuraminic acid (Neu5Ac) analogues have been made in an efficient manner, four of which are series of naturally occurring 4-O-acetylated containing Neu5Ac.  The chemical understandings of these compounds can provide further knowledge in biological functions and structural dynamics of sialic acids including its role in immunogenic properties of mammalian cells.

Series of partially O-acetylated N-acetyl neuraminic acid (Neu5Ac) using regioselective silyl exchange technology (ReSET)

248th National Meeting (2014)

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