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Solution Structures and Molecular Associations of a Peptide-Based Catalyst for the Stereoselective Baeyer-Villiger Oxidation.

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.

SUBMITTER: Abascal NC

PROVIDER: S-EPMC5130343 | biostudies-literature | 2016 Sep

REPOSITORIES: biostudies-literature

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Solution Structures and Molecular Associations of a Peptide-Based Catalyst for the Stereoselective Baeyer-Villiger Oxidation.

Abascal Nadia C NC Miller Scott J SJ

Organic letters 20160902 18

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 dy ...[more]

PMID: 27588823

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