Sialic acids are an extremely important class of sugars which are involved in numerous biological phenomena. As a consequence, sialylation has become the most important reaction in sialic acid chemistry. However, a complete mechanistic rationale has yet to be described, resulting in empiricism and slow development of this important area. To address this problem, relative kinetic studies, specifically cation clock kinetic studies were done on the sialylation reaction. In this study, the C-1 position of sialic acid was modified with <i>O</i>-xylylene ester and used in the N-Ac protected a- and b- sialyl donors, N-Ac-oxazolidinone and NCS protected β- sialyl donors to investigate the effect of glycosyl acceptor concentration on sialylation reaction. Further, the effect of temperature on selectivity of sialylation reaction was examined. In addition, the influence of acetonitrile as a co-solvent in the presence of dichloromethane was investigated.

Probing the mechanism of sialidation reactions via cation clock kinetics

252nd National Meeting (2016)

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