Evaluation of α-pyrones and pyrimidones as photoaffinity probes for affinity-based protein profiling.

Oliver A Battenberg, Matthew B Nodwell, Stephan A Sieber

Department Chemie, Center for Integrated Protein Science CIPSM, Institute of Advanced Studies, Technische Universität München, Lichtenbergstrasse 4, 85747 Garching, Germany.

The Journal of organic chemistry 2011 Aug 5

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α-Pyrones and pyrimidones are common structural motifs in natural products and bioactive compounds. They also display photochemistry that generates high-energy intermediates that may be capable of protein reactivity. A library of pyrones and pyrimidones was synthesized, and their potential to act as photoaffinity probes for nondirected affinity-based protein profiling in several crude cell lysates was evaluated. Further "proof-of-principle" experiments demonstrate that a pyrimidone tag on an appropriate scaffold is equally capable of proteome labeling as a benzophenone.

Citation

Oliver A Battenberg, Matthew B Nodwell, Stephan A Sieber. Evaluation of α-pyrones and pyrimidones as photoaffinity probes for affinity-based protein profiling. The Journal of organic chemistry. 2011 Aug 5;76(15):6075-87