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- W2051839679 abstract "Density functional theory using B3LYP and flexible ligand docking methods were used to investigate the complete potential surface for the uncatalyzed and the AZ28 antibody-catalyzed oxy-Cope reaction of 2,5-diaryl-1,5-hexadien-3-ol derivatives. The reaction mechanism is stepwise, involving a cyclohexane diyl intermediate. Theoretical deuterium isotope effects match well with those from experiment. Gas-phase transition structures show mixed preferences for the axial vs equatorial hydroxyl group, while solvation favors the axial isomer. Specific phenyl group conformations are shown to be critical to transition-state stabilization (by up to 15 kcal/mol), and the effective conformation is not that found in the hapten used to generate the germline and affinity-matured AZ28 catalytic antibodies. Docking studies support greater transition-state binding than reactant binding. Docking studies also predict the S stereoselectivity of mature AZ28 and suggest that binding modes quite different from those of the hapten might play a role in catalysis, with specific focus on ligand hydrogen bonding to Asp(H101)." @default.
- W2051839679 created "2016-06-24" @default.
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- W2051839679 date "2004-07-10" @default.
- W2051839679 modified "2023-10-01" @default.
- W2051839679 title "Antibody-Catalyzed Oxy-Cope Rearrangement: Mechanism and Origins of Catalysis and Stereoselectivity from DFT Quantum Mechanics and Flexible Docking" @default.
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- W2051839679 doi "https://doi.org/10.1021/ja048604g" @default.
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