An Epoxide Intermediate in Glycosidase Catalysis
L.F. Sobala, Gaetano Speciale, Sha Zhu, Lluı́s Raich, Natalia Sannikova, Andrew J. Thompson, Z. Hakki, Dan Lu, Saeideh Shamsi Kazem Abadi, Andrew R. Lewis, V. Rojas-Cervellera, Ganeko Bernardo‐Seisdedos, Yongmin Zhang, Óscar Millet, Jesús Jiménez‐Barbero, Andrew J. Bennet, Matthieu Sollogoub, Carme Rovira, G.J. Davies, Spencer J. Williams
Abstract
O (1.052 ± 0.006) directly implicates nucleophilic participation by the C2-hydroxyl. Collectively, these data substantiate this unprecedented and long-imagined enzymatic mechanism.
Topics & Concepts
ChemistryAnomerStereochemistryNucleophileGlycoside hydrolaseLeaving groupOxocarbeniumEnzyme catalysisGlycosylEpoxideHydrolysisCatalysisOrganic chemistryCarbohydrate Chemistry and SynthesisEnzyme Production and CharacterizationEnzyme Structure and Function