Aldol reactions are central carbon-carbon bond forming reactions that have been used in the synthesis of many biologically active compounds. For aldol and other reactions, there is interest in the development of peptide catalysts due to their chemical robustness, potential for asymmetric catalysis, and modular synthesis. To analyze the activity of the numerous potential catalytic peptide sequences that are readily accessible, we have worked towards the development of a colorimetric-displacement assay for the evaluation of catalytic activity. Specifically, we have adapted a diol-detecting indicator displacement assay for the measurement of diol product from an aldol reaction such that an absorbance change in the dye correlates with the catalytic activity of the potential peptide catalysts. After initially validating the system, we are now adapting the assay to a multiwell plate format for higher-throughput analysis. This rapid assay for catalytic activity will enable us to study numerous sequences, such as those containing beta-turn motifs, to identify highly active peptide catalysts and to obtain a greater understanding of sequence-activity relationships.

Development of a colorimetric displacement assay for the evaluation of peptide aldol catalysts

2019 Spring National Meeting

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