title: 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.
authors.affiliation: Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, MI 48202, USA.
authors.forename: Pavan K
authors.initials: PK
authors.lastname: Kancharla
authors.forename: Chandrasekhar
authors.initials: C
authors.lastname: Navuluri
authors.forename: David
authors.initials: D
authors.lastname: Crich
mesh_terms: D002254:Carbonates / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D019158:N-Acetylneuraminic Acid / Q000138:chemical synthesis / Q000737:chemistry*; D023303:Oxazolidinones / Q000737:chemistry*
chemical_list: D002254:Carbonates; D006027:Glycosides; D023303:Oxazolidinones; D019158:N-Acetylneuraminic Acid