Protein Modification via Mild Photochemical Isomerization of Triazenes to Release Aryl Diazonium Ions

Garrett J. Davis, Julia A. Townsend, Madeline G. Morrow, Mohamed Hamie, Abigail J. Shepard, Chih Chieh Hsieh, Michael T. Marty, John C. Jewett

Research output: Contribution to journalArticlepeer-review

Abstract

This work describes the development of phenyl diazenyl piperidine triazene derivatives that can be activated to release aryl diazonium ions for labeling of proteins using light. These probes show marked bench stability at room temperature and can be photoisomerized via low-intensity UVA irradiation at physiological pH. Upon isomerization, the triazenes are rendered more basic and readily protonate to release reactive aryl diazonium ions. It was discovered that the intensity and duration of the UV light was essential to the observed diazonium ion reactivity in competition with the traditionally observed photolytic radical pathways. The combination of their synthetic efficiency coupled with their overall stability makes triazenes an attractive candidate for use in bioconjugation applications. Bioorthogonal handles on the triazenes are used to demonstrate the ease by which proteins can be modified.

Original languageEnglish (US)
Pages (from-to)2432-2438
Number of pages7
JournalBioconjugate Chemistry
Volume32
Issue number11
DOIs
StatePublished - Nov 17 2021

ASJC Scopus subject areas

  • Biotechnology
  • Bioengineering
  • Biomedical Engineering
  • Pharmacology
  • Pharmaceutical Science
  • Organic Chemistry

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