An Efficient Solid‐Phase Synthetic Approach to Prepare TACN‐Functionalized Peptides

Yik‐Hoi Yeung, Pak‐Lun Lam, Waygen Thor, Hei‐Yui Kai, Tsz‐Lam Cheung, Yue Wu*, Ga‐Lai Law*, Nicholas J. Long*, Ka‐Leung Wong*

*Corresponding author for this work

Research output: Contribution to journalJournal articlepeer-review

1 Citation (Scopus)

Abstract

1,4,7-triazacyclononane (TACN) derivatives play important roles in various metal-based biomedical applications. However, the unmanageable functionalization of TACN remains a long-standing challenge to yield useful partially substituted building blocks. Herein, by utilizing nitrobenzoxadiazole (NBD) as a thiol-liable protecting group for secondary amines, a bis-NBD-substituted TACN was obtained as the first example in the preparation of partially substituted TACN without strict stoichiometric control and column chromatography. Upon facile deprotection of NBD using solid-phase synthesis, a series of TACN-peptide conjugates with different bioactive peptides and chelating units were derivatized from the TACN building block, demonstrating the potential widespread application of this work.
Original languageEnglish
Article numbere202400053
Number of pages5
JournalChemistry-Methods
Volume5
Issue number5
Early online date3 Feb 2025
DOIs
Publication statusPublished - May 2025

User-Defined Keywords

  • 1,4,7-Triazacyclononane (TACN)
  • nitrobenzoxadiazole (NBD)
  • peptide conjugates
  • Positron Emission Tomography (PET)
  • protecting group

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