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Macrocyclization of bioactive peptides with internal thiazole motifs via palladium-catalyzed C-H olefination.

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Peptides containing thiazole fragments represent a large group of bioactive compounds with potential medicinal applications. However, methods for efficient synthesis of these compounds with structural diversity are limited. Herein, we… Click to show full abstract

Peptides containing thiazole fragments represent a large group of bioactive compounds with potential medicinal applications. However, methods for efficient synthesis of these compounds with structural diversity are limited. Herein, we report a method for modification and macrocyclization of thiazole-containing peptides through palladium-catalyzed δ-C(sp2)-H olefination. In this protocol, the thiazole and neighboring amide bonds act as directing groups, which allows site-specific olefination of phenylalanine, tryptophan and tyrosine residues. This chemistry exhibits broad substrate scope and provides facile access to peptide-peptide conjugates and peptide macrocycles. Our results highlight the potency and applicability of thiazole motifs in promoting Pd-catalyzed functionalization of peptides.

Keywords: macrocyclization bioactive; thiazole motifs; palladium catalyzed; olefination

Journal Title: Chemical communications
Year Published: 2022

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