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Dissecting the Influence of Oxazolidinones and Cyclic Carbonates in Sialic Acid Chemistry
Author(s) -
Kancharla Pavan K.,
Navuluri Chandrasekhar,
Crich David
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201204400
Subject(s) - chemistry , pyranose , sialic acid , ring (chemistry) , anomer , dipole , stereochemistry , protonation , glycosylation , computational chemistry , organic chemistry , biochemistry , ion
At a moment′s notice : Thermal equilibration of 1 and mass spectral analysis of sialyl phosphates suggest that the 4 O ,5 N ‐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.