Laboratory of Catalysis and Organic Synthesis (LCSO), Ecole Polytechnique Fédérale de Lausanne, EPFL, 1015, Lausanne, Switzerland.
Angew Chem Int Ed Engl. 2024 Aug 12;63(33):e202404747. doi: 10.1002/anie.202404747. Epub 2024 Jul 11.
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.
苯并[1,3]间二氧杂环戊烯并[5,6-h]吲哚啉（EB(X)xs）试剂由于其多样的反应性和高选择性，已成为用于肽/蛋白质修饰的有用试剂。在此，我们报告了在不同的氨基酸砌块（Lys/Orn/Dap）上成功引入苯并[1,3]间二氧杂环戊烯并[5,6-h]吲哚啉（EBxs），并展示了它们与固相肽合成（SPPS）和溶液相肽合成（SPS）的兼容性。EBx 核选择性地掺入到肽序列中，可在温和条件下有效地进行大环化反应，从而合成拓扑独特的环状和双环肽。
