1,2,3-Triazole-containing azamacrocycles from chiral triazolopeptoids: synthesis and solid-state studies

Chemistry. 2024 May 3:e202400904. doi: 10.1002/chem.202400904. Online ahead of print.ABSTRACTTwo new chiral 1,2,3-triazole-containing macrocyclic oligoamides (i.e.: triazolopeptoid 4 and 5) were obtained through solid-phase synthesis of linear precursors followed by high dilution macrocyclization reaction. Theoretical (DFT) and spectroscopic (NMR) studies revealed the intricate interplay between the Na-chiral side chains and their conformational attitudes. BH3-mediated reduction of the tertiary amide groups of known 1-3 and newly synthesized 4 gave novel azamacrocycles 6-9. Detection of borane complexes of azamacrocycles 6 and 9 (i.e.: 10 and 11), corroborated by X-ray diffraction studies, demonstrated the peculiar properties of 1,2,3-triazole-containing macrorings.PMID:38699895 | DOI:10.1002/chem.202400904

Source: Chemistry - May 3, 2024 Category: Chemistry Authors: Alicja Araszczuk Giovanni Pierri Rosaria Schettini Chiara Costabile Giorgio Della Sala Luca Di Marino Consiglia Tedesco Francesco De Riccardis Irene Izzo Source Type: research