4.8 Article

Palladium-Catalyzed Aminocarbonylation in Solid-Phase Peptide Synthesis: A Method for Capping, Cyclization, and Isotope Labeling

Journal

ORGANIC LETTERS
Volume 19, Issue 11, Pages 2873-2876

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b01068

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Funding

  1. Anna Maria Lundin Travel Grant (Smalands Nation)
  2. Danish National Research Foundation [DNRF118]
  3. Villum Foundation
  4. Danish Council for Independent Research: Technology and Production Sciences

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A new synthetic approach for introducing N-capping, groups onto peptides attached to a solid support, Combining aminocarbonylation under mild conditions Wing a palladacycle precatalyst and, solid-phase peptide synthesis is reported. The use of la silacarboxylic acid as an in situ CO-releasing molecule allowed the reaction to be performed single vial. The method also enables versatile substitution of side chains, side-chain to side-chain cyclizations, and selective aryl labeling of modified peptides.

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