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Solid-Phase Peptide Macrocyclization and Multifunctionalization via Dipyrrin Construction.

ABSTRACT: We introduce a new and highly efficient synthetic protocol towards multifunctional fluorescent cyclopeptides by solid-phase peptide macrocyclization via dipyrrin construction, with full scope of proteinogenic amino acids and different ring sizes. Various bicyclic peptides can be created by dipyrrin-based crosslinking and double dipyrrin-ring formation. The embedded dipyrrin can be either transformed to fluorescent BODIPY and then utilized as cancer-selective targeted protein imaging probe in vitro, or directly employed as a selective metal sensor in aqueous media. This work provides a valuable addition to the peptide macrocyclization toolbox, and a blueprint for the development of multifunctional dipyrrin linkers in cyclopeptides for a wide range of potential bioapplications.

SUBMITTER: Wu Y

PROVIDER: S-EPMC8457249 | biostudies-literature | 2021 Sep

REPOSITORIES: biostudies-literature

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Solid-Phase Peptide Macrocyclization and Multifunctionalization via Dipyrrin Construction.

Wu Yue Y Chau Ho-Fai HF Thor Waygen W Chan Kaitlin Hao Yi KHY Ma Xia X Chan Wai-Lun WL Long Nicholas J NJ Wong Ka-Leung KL

Angewandte Chemie (International ed. in English) 20210806 37

We introduce a new and highly efficient synthetic protocol towards multifunctional fluorescent cyclopeptides by solid-phase peptide macrocyclization via dipyrrin construction, with full scope of proteinogenic amino acids and different ring sizes. Various bicyclic peptides can be created by dipyrrin-based crosslinking and double dipyrrin-ring formation. The embedded dipyrrin can be either transformed to fluorescent BODIPY and then utilized as cancer-selective targeted protein imaging probe in vit ...[more]

PMID: 34272794

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