Biocompatible synthesis of macrocyclic thiazole peptides from chiral α-amino nitriles

Shang, MinghaoHe, JunmingGardiner, Michael G.Nitsche, Christoph2025-06-122025-06-121477-0520WOS:001390652000001PubMed:39775491ORCID:/0000-0002-3704-2699/work/176533592https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=anu_research_portal_plus2&SrcAuth=WosAPI&KeyUT=WOS:001390652000001&DestLinkType=FullRecord&DestApp=WOS_CPLhttps://hdl.handle.net/1885/733759891Macrocyclic peptides containing a thiazole heterocycle exhibit fascinating properties in natural products and future therapeutics. We report a biocompatible macrocyclisation approach facilitated by an N-terminal cysteine and C-terminal nitriles. The use of various chiral alpha-amino nitriles enables the incorporation of diverse hydrophobic side chains adjacent to the thiazole motif.CN thanks the Australian Research Council for funding support, including a Discovery Project (DP230100079) and Future Fellowship (FT220100010). We thank Dr Douglas Lawes (ANU) for assistance in recording NMR spectra.4enCyclic peptideHexapeptidesBiocompatible synthesis of macrocyclic thiazole peptides from chiral α-amino nitriles202410.1039/d4ob01989j85214585446