Versatile Synthesis of Multivalent Porphyrin–Peptide Conjugates by Direct Porphyrin Construction on Resin

Yue Wu, Ho Fai Chau, Yik Hoi Yeung, Waygen Thor, Hei Yui Kai, Wai Lun Chan*, Ka Leung Wong*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

Multifunctional porphyrin–peptide conjugates with different propensities for self-assembly into various supramolecular nanoarchitectures play important roles in advanced materials and biomedical research. However, preparing prefunctionalized core porphyrins by traditional low-yielding statistical synthesis and purifying them after peptide ligation through many rounds of HPLC purification is tedious and unsustainable. Herein, we report a novel integrated solid-phase synthetic protocol for the construction of porphyrin moieties from simple aldehydes and dipyrromethanes on resin-bound peptides directly to form mono-, cis/trans-di-, and trivalent porphyrin–peptide conjugates in a highly efficient and controllable manner; moreover, only single final-stage HPLC purification of the products is needed. This efficient strategy enables the rapid, greener, and substrate-controlled diversity-oriented synthesis of multivalent porphyrin-(long) peptide conjugate libraries for multifarious biological and materials applications.
Original languageEnglish
Article numbere202207532
Number of pages9
JournalAngewandte Chemie. International Edition
Volume61
Issue number34
Early online date22 Jun 2022
DOIs
Publication statusPublished - 22 Aug 2022

Scopus Subject Areas

  • Chemistry(all)
  • Catalysis

User-Defined Keywords

  • Fluorescent Peptides
  • Multivalent Porphyrin–Peptide Conjugates
  • Porphyrins
  • Solid-Phase Peptide Synthesis
  • Targeted Bioimaging

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