Hypervalent Iodine Amino Acid Building Blocks for Bioorthogonal Peptide Macrocyclization.

Angew Chem Int Ed Engl

Laboratory of Catalysis and Organic Synthesis (LCSO), Ecole Polytechnique Fédérale de Lausanne, EPFL, 1015, Lausanne, Switzerland.

Published: August 2024


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Article Abstract

Ethynylbenziodoxol(on)es (EB(X)xs) reagents have emerged as useful reagents for peptide/protein modification due to their versatile reactivity and high selectivity. Herein, we report the successful introduction of ethynylbenziodoxoles (EBxs) on different amino acid building blocks (Lys/Orn/Dap), and show their compatibility with both solid phase peptide synthesis (SPPS) and solution phase peptide synthesis (SPS). The selective incorporation of the EBx core into peptide sequences enable efficient macrocyclizations under mild conditions for the synthesis of topologically unique cyclic and bicyclic peptides.

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http://dx.doi.org/10.1002/anie.202404747DOI Listing

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