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• W3081961888 endingPage "16973" @default.
• W3081961888 startingPage "16965" @default.
• W3081961888 abstract "Carbohydrate side chain conformation confers a significant influence on reactivity during glycosylation and anomeric bond hydrolysis due to stabilization of the oxocarbenium-like transition state. By analysis of 513 pyranoside-bound glycoside hydrolase (GH) crystal structures, we determine that most glucosidases and β-mannosidases preferentially bind their substrates in the most reactive gauche,gauche (gg) conformation, thereby maximizing stabilization of the corresponding oxocarbenium ion-like transition state during hydrolysis. α-Galactoside hydrolases mostly show a preference for the second most activating gauche,trans (gt) conformation to avoid the energy penalty that would arise from imposing the gg conformation on galacto-configured ligands. These preferences stand in stark contrast to the side chain populations observed for these sugars both in free solution and bound to nonhydrolytic proteins, where for the most part a much greater diversity of side chain conformations is observed. Analysis of sequences of GH–ligand complexes reveals that side chain restriction begins with the enzyme–substrate complex and persists through the transition state until release of the hydrolysis product, despite changes in ring conformation along the reaction coordinate. This work will inform the design of new generations of glycosidase inhibitors with restricted side chains that confer higher selectivity and/or affinity." @default.
• W3081961888 created "2020-09-08" @default.
• W3081961888 creator A5027175360 @default.
• W3081961888 creator A5074473176 @default.
• W3081961888 date "2020-09-02" @default.
• W3081961888 modified "2023-10-17" @default.
• W3081961888 title "Glycoside Hydrolases Restrict the Side Chain Conformation of Their Substrates To Gain Additional Transition State Stabilization" @default.
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• W3081961888 doi "https://doi.org/10.1021/jacs.0c05592" @default.
• W3081961888 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/7544649" @default.
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• W3081961888 hasPublicationYear "2020" @default.
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