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Dissecting the Influence of Oxazolidinones and Cyclic Carbonates in Sialic Acid Chemistry

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  • We thank the NIH (GM 62160) for support of this work.

Abstract

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At a moment′s notice: Thermal equilibration of 1 and mass spectral analysis of sialyl phosphates suggest that the 4O,5N-oxazolidinone and the 4,5-O-carbonate systems influence the anomeric effect and the mechanisms of sialidation by virtue of their dipole moment in the mean plane of the pyranose ring. The electron-withdrawing effect destabilizes 2 and promotes associative glycosylation mechanisms. TEMPO=2,2,6,6-tetramethylpiperidine N-oxide.

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