Photocleavable Protecting Groups Using a Sulfite Self-Immolative Linker for High Uncaging Quantum Yield and Aqueous Solubility

Albert Marten Schulte, Quentin Vivien, Julia H Leene, Georgios Alachouzos, Ben L Feringa*, Wiktor Szymanski*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

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Abstract

Using light as an external stimulus to control (bio)chemical processes offers many distinct advantages. Most importantly, it allows for spatiotemporal control simply through operating the light source. Photocleavable protecting groups (PPGs) are a cornerstone class of compounds that are used to achieve photocontrol over (bio)chemical processes. PPGs are able to release a payload of interest upon light irradiation. The successful application of PPGs hinges on their efficiency of payload release, captured in the uncaging Quantum Yield (QY). Heterolytic PPGs efficiently release low pKa payloads, but their efficiency drops significantly for payloads with higher pKa values, such as alcohols. For this reason, alcohols are usually attached to PPGs via a carbonate linker. The self-immolative nature of the carbonate linker results in concurrent release of CO2 with the alcohol payload upon irradiation. We introduce herein novel PPGs containing sulfites as self-immolative linkers for photocaged alcohol payloads, for which we discovered that the release of the alcohol proceeds with higher uncaging QY than an identical payload released from a carbonate-linked PPG. Furthermore, we demonstrate that uncaging of the sulfite-linked PPGs results in the release of SO2 and show that the sulfite linker improves water solubility as compared to the carbonate-based systems.
Original languageEnglish
Article numbere202411380
Number of pages10
JournalAngewandte Chemie (International ed. in English)
Volume63
Issue number47
Early online date14-Oct-2024
DOIs
Publication statusE-pub ahead of print - 14-Oct-2024

Keywords

  • Photocleavable protecting groups
  • Linkers
  • Alcohol payloads
  • Anion Stabilization
  • Quantum Yield

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