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Dr. Pavan K. Kancharla, Chandrasekhar Navuluri and Prof. Dr. David Crich Dissecting the Influence of Oxazolidinones and Cyclic Carbonates in Sialic Acid Chemistry Angewandte Chemie International Edition 51

Article first published online: 13 SEP 2012 | DOI: 10.1002/anie.201204400

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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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