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Dissecting the influence of oxazolidinones and cyclic carbonates in sialic acid chemistry.

ABSTRACT: 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.

SUBMITTER: Kancharla PK

PROVIDER: S-EPMC3489474 | biostudies-literature | 2012 Oct

REPOSITORIES: biostudies-literature

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Dissecting the influence of oxazolidinones and cyclic carbonates in sialic acid chemistry.

Kancharla Pavan K PK Navuluri Chandrasekhar C Crich David D

Angewandte Chemie (International ed. in English) 20120913 44

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. ...[more]

PMID: 22976809

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