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Peptide Fragment Coupling Using a Continuous-Flow Photochemical Rearrangement of Nitrones

Authors


  • We are grateful to the Novartis-MIT Center for Continuous Manufacturing for financial support. We thank several colleagues at MIT (Dr. Andrew S. Kleinke, Dr. James J. Mousseau, Dr. Ping Zhang, and Kurt Armbrust) and at Novartis (Dr. Guido Koch, Dr. Berthold Schenkel, Dr. Gerhard Penn, Dr. Benjamin Martin, and Dr. Jörg Sedelmeier) for insightful discussions. We also thank Eric Standley (MIT) and Li Li (MIT) for obtaining mass spectrometric data.

Abstract

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Go with the flow: A general approach for amide bond formation by way of a continuous-flow photochemical rearrangement of nitrones was described (see scheme). Simple aryl-alkyl amide bonds as well as complex peptide bonds were constructed efficiently with a residence time less than 20 minutes. A tetrapeptide was synthesized in this way and the method could be applied to peptide fragment coupling.

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