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Solution Structures and Molecular Associations of a Peptide-Based Catalyst for the Stereoselective Baeyer-Villiger
Nadia C Abascal1, Scott J Miller1
1Department of Chemistry, Yale University , New Haven, Connecticut 026520-8107, United States.
Abstract:
The structural analysis of a peptide-based catalyst for the Baeyer-Villiger oxidation (BVO) is reported. This unique structure is then analyzed in the context of its previously documented facility to control selectivity (both enantioselectivity and migratory aptitude) in catalytic reactions. The effects of additives on the solution conformation of the peptide are found to be dramatic, revealing substrate-specific interactions and a possible "induced fit" model. The experimental observation of dynamic behavior supports the notion that flexibility in stereoselective catalysts can be an advantageous feature.
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