Work

A Synergistic Combinatorial and Chiroptical Study of Peptide Catalysts for Asymmetric Baeyer–Villiger Oxidation

Year: 2015

Type: article

Abstract: We report an approach to the asymmetric Baeyer-Villiger oxidation utilizing bioinformatics-inspired combinatorial screening for catalyst discovery. Scaled-up validation of our on-bead efforts with a circular dichroism-based assay of alcohols derived from the products of solution-phase reactions established the absolute configuration of lactone products; this assay proved equivalent to HPLC in its ability to evaluate catalyst performance, but was far superior in its speed of analysis. Further solution-phase screening of a focused library suggested a mode of asymmetric induction that draws distinct parallels with the mechanism of Baeyer-Villiger monooxygenases.

Source: Advanced Synthesis & Catalysis

DOI: 10.1002/adsc.201500230

Authors: Michael W. Giuliano, Chung‐Yon Lin, David K. Romney, Scott J. Miller, Eric V. Anslyn

Institutions: Yale University, The University of Texas at Austin

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Yale University, National Institutes of Health, National Institute of General Medical Sciences

Awards: Further Improving and Utilizing HTS Methods for EE Determinations, Selective Peptide-Based Oxidation Catalysts for Bioactive Molecule Synthesis