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

Kancharla Pavan K. | Zendy; Navuluri Chandrasekhar | Zendy; Crich David | Zendy

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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.

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