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

Organic Letters
Anna SkoghAnja Sandström

Abstract

A new synthetic approach for introducing N-capping groups onto peptides attached to a solid support, combining aminocarbonylation under mild conditions using a palladacycle precatalyst and solid-phase peptide synthesis, is reported. The use of a silacarboxylic acid as an in situ CO-releasing molecule allowed the reaction to be performed in a single vial. The method also enables versatile substitution of side chains, side-chain-to-side-chain cyclizations, and selective [13C] acyl labeling of modified peptides.

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Citations

Jun 3, 2018·Journal of Labelled Compounds & Radiopharmaceuticals·Dennis U NielsenTroels Skrydstrup
Aug 1, 2018·Chemistry, an Asian Journal·Yogesh G ShelkeAnant R Kapdi
May 14, 2019·Organic & Biomolecular Chemistry·Krishanu MondalParthasarathi Das
Dec 4, 2019·Macromolecular Rapid Communications·Fadi ShamoutLaura Hartmann
May 16, 2020·Chemical Communications : Chem Comm·Zhengkai ChenXiao-Feng Wu

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