Peptide stapling by late-stage Suzuki–Miyaura cross-coupling

• Hendrik Gruß,
• Rebecca C. Feiner,
• Ridhiwan Mseya,
• David C. Schröder,
• Michał Jewgiński,
• Kristian M. Müller,
• Rafał Latajka,
• Antoine Marion and
• Norbert Sewald

Beilstein J. Org. Chem. 2022, 18, 1–12, doi:10.3762/bjoc.18.1

• its native binding partner β-catenin. An increased proteolytic stability against proteinase K has been demonstrated. Keywords: accelerated molecular dynamics; halotryptophan; intrinsically disordered peptides; late-stage diversification; macrocyclisation; molecular dynamics; stapled peptides; Suzuki

• stapling and the most prominent methodology was developed by the groups of Grubbs and Verdine using ring-closing metathesis (RCM) [4][5][6]. The optimised protocol for these so-called hydrocarbon-stapled peptides uses α-methyl-, α-alkenylglycines in a distance of i, i + 3/i + 4 for one helix turn or i, i

• + 7 for two helix turns, respectively, followed by Ru-catalysed cross-linking [7]. By this robust and reliable approach, a library of stapled peptides was generated influencing diverse α-helical dominated protein–protein interactions (PPI) spanning pathways involved in cancer, infectious diseases

Aqueous olefin metathesis: recent developments and applications

• Valerio Sabatino and
• Thomas R. Ward

Beilstein J. Org. Chem. 2019, 15, 445–468, doi:10.3762/bjoc.15.39

• exploit biocompatible conditions. This review focuses on the progress made in aqueous olefin metatheses and their applications in chemical biology. Keywords: aqueous catalysis; artificial metalloenzymes; chemical biology; green chemistry; olefin metathesis; ruthenium catalysts; stapled peptides

• -metathesis reaction of allyl sulfide 99. Preparation of BODIPY-containing profluorescent probes 102 and 104. Metathesis-based ethylene detection in live cells. First example of stapled peptides via olefin metathesis. RCM of challenging substrate 17 in air and in the presence of water. RCM of N,N