Premium
A Free‐Energy Relationship between the Rate of Acidic Hydrolysis of Glycosides and the p K a of Isofagomines
Author(s) -
Jensen Henrik H.,
Lyngbye Laila,
Bols Mikael
Publication year - 2001
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 - 10.1002/1521-3773(20010917)40:18<3447::aid-anie3447>3.0.co;2-8
Subject(s) - glycoside , hydrolysis , chemistry , stereochemistry , organic chemistry
A new answer to a 100‐year‐old puzzle is presented here, namely, why are galactosides hydrolyzed faster than glucosides? This disparity was long attributed to facilitation by axial OH groups of a conformational change en route to the transition state. However, the results presented here indicate that differences in the electron‐withdrawing effects (represented by arrows) of equatorial ( A ) and axial OH groups ( B ) are decisive.