Synthesis of N-isoindolinonyl peptides via Pd-catalyzed C(sp2)-H olefination-activation and their conformational studies.

Isoindolinone is a constituent of several natural products that show a wide range of bioactivity, such as anticancer, antimicrobial, antiviral and anti-inflammatory properties. It would be interesting to explore the carbonyl group (H-bond acceptor) of isoindolinone and its structural and conformational changes. However, the synthesis of isoindolinone-comprising peptides in short steps is challenging. Herein, we have developed a synthetic methodology for introducing the isoindolinone residue to peptides via Pd-catalyzed C(sp2)-H activation/olefination, and demonstrated the conformational changes owing to the isoindolinone scaffold. Hence, isoindolinonyl peptides provide an avenue for the synthesis of novel foldamers and therapeutic agents.

Citation

Manish K Gupta, Ankita Panda, Subhasish Panda, Nagendra K Sharma. Synthesis of N-isoindolinonyl peptides via Pd-catalyzed C(sp2)-H olefination-activation and their conformational studies. Organic & biomolecular chemistry. 2023 Jun 21;21(24):5104-5116

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PMID: 37278539

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