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Non-benzenoid N -aryl oxalamide: synthesis of troponyl-oxalamide peptides by Pd(II)-catalyzed C(sp 3 )-H functionalization of glycinamides.
- Source :
-
Organic & biomolecular chemistry [Org Biomol Chem] 2024 Aug 22; Vol. 22 (33), pp. 6822-6832. Date of Electronic Publication: 2024 Aug 22. - Publication Year :
- 2024
-
Abstract
- Aryl oxalamides are constituents of various promising drug-like molecules. Their aryl groups are derived from the benzenoid aromatic moiety. However, non-benzenoid aromatic molecules, troponoids, are found in various bioactive natural products. It would be thought-provoking to explore non-benzenoid aryl oxalamide derivatives. This report describes the synthesis of N -troponyl-oxalamide peptides by Pd(II)-catalyzed C(sp <superscript>3</superscript> )-H functionalization of N -troponyl glycinate peptides. This is the first instance of β-hydride elimination at the palladium complex of N -troponyl glycinates that generates imine in situ , rendering the synthesis of oxalamides. Importantly, the crystal structures of representative oxalamide derivatives form distinctive foldameric structures, such as β-sheet type structures, owing to the presence of additional troponyl carbonyl groups. Hence, these non-benzenoid oxalamides are potential scaffolds for tuning the structure and function of N -troponyl peptides, which could provide innovative avenues of research in the development of emerging structural and functional peptides.
Details
- Language :
- English
- ISSN :
- 1477-0539
- Volume :
- 22
- Issue :
- 33
- Database :
- MEDLINE
- Journal :
- Organic & biomolecular chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 39114897
- Full Text :
- https://doi.org/10.1039/d4ob00800f