Solid-Phase Peptide Macrocyclization and Multifunctionalization via Dipyrrin Construction

Yue Wu, Ho Fai Chau, Waygen Thor, Kaitlin Hao Yi Chan, Xia Ma, Wai Lun Chan*, Nicholas J. Long*, Ka Leung Wong*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)20301-20307
Number of pages7
JournalAngewandte Chemie - International Edition
Volume60
Issue number37
DOIs
Publication statusPublished - 6 Sep 2021

Scopus Subject Areas

  • Catalysis
  • Chemistry(all)

User-Defined Keywords

  • dipyrrin
  • fluorescent cyclic peptides
  • solid-phase peptide synthesis
  • zinc(II) sensing
  • αvβ3 imaging

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