Direct Construction of Corrole-peptide Conjugates by Controllable Bilane Formation on Resin

Yue Wu, Ho-Fai Chau, Hei-Yui Kai, Wing-Sze Tam, Yik-Hoi Yeung, Waygen Thor, Tsz-Lam Cheung, Chen Xie, Jing-Xiang Zhang, Ka-Leung Wong*

*Corresponding author for this work

Research output: Contribution to journalJournal articlepeer-review

Abstract

Corroles have attracted increasing research interests in recent decades owing to their unique properties over porphyrins. However, the relatively inefficient and tedious synthetic procedures of corrole building blocks with functional groups for bioconjugation hindered their bioapplications. Herein, we report a highly efficient protocol to synthesize corrole-peptide conjugates with good yields (up to 63 %) without using prepared corrole building blocks. By condensing two -COOH-bearing-dipyrromethane molecules onto an aldehyde group on resin-bound peptide chains in a controllable manner, a series of desired products with long (up to 25 residues) and bioactive peptide chains were obtained with at most one chromatographic purification. The synthesized compounds exhibited potential applications as chelators for metal ions for biomedical applications, as building blocks for supramolecular materials, as well as targeted fluorescent probes.
Original languageEnglish
Article numbere202203623
Number of pages7
JournalChemistry - A European Journal
Volume29
Issue number25
Early online date19 Feb 2023
DOIs
Publication statusPublished - 2 May 2023

Scopus Subject Areas

  • Chemistry(all)
  • Catalysis
  • Organic Chemistry

User-Defined Keywords

  • Corrole
  • Corrole-peptide conjugates
  • Latent membrane protein 1
  • Solid-phase peptide synthesis
  • Targeted Bioimaging

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