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

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 number e202207532
JournalAngewandte Chemie. International Edition
DOIs
Publication statusE-pub ahead of print - 22 Jun 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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