Issue 24, 2023

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

Abstract

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
12 May 2023
Accepted
22 May 2023
First published
23 May 2023

Org. Biomol. Chem., 2023,21, 5104-5116

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

M. K. Gupta, A. Panda, S. Panda and N. K. Sharma, Org. Biomol. Chem., 2023, 21, 5104 DOI: 10.1039/D3OB00742A

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