Porphyrin as a versatile visible-light-activatable organic/metal hybrid photoremovable protecting group.

Autor: Sekhar AR; School of Plant Sciences and Food Security, Faculty of Life Sciences, Tel-Aviv University, Tel-Aviv, 6997801, Israel., Chitose Y; Department of Chemistry, Faculty of Science, Masaryk University, Kamenice 5, 625 00, Brno, Czech Republic.; RECETOX, Faculty of Science, Masaryk University, Kamenice 5, 625 00, Brno, Czech Republic.; Basic Chemistry Program, Graduate School of Advanced Science and Engineering, Hiroshima University, Higashi-Hiroshima, 739-8526, Japan., Janoš J; Department of Physical Chemistry, University of Chemistry and Technology, Prague, Technická 5, 16628, Prague 6, Czech Republic., Dangoor SI; Department of Physiology and Pharmacology, Sackler School of Medicine, Tel Aviv University, 6997801, Tel Aviv, Israel., Ramundo A; Department of Chemistry, Faculty of Science, Masaryk University, Kamenice 5, 625 00, Brno, Czech Republic.; RECETOX, Faculty of Science, Masaryk University, Kamenice 5, 625 00, Brno, Czech Republic., Satchi-Fainaro R; Department of Physiology and Pharmacology, Sackler School of Medicine, Tel Aviv University, 6997801, Tel Aviv, Israel., Slavíček P; Department of Physical Chemistry, University of Chemistry and Technology, Prague, Technická 5, 16628, Prague 6, Czech Republic., Klán P; Department of Chemistry, Faculty of Science, Masaryk University, Kamenice 5, 625 00, Brno, Czech Republic. klan@sci.muni.cz.; RECETOX, Faculty of Science, Masaryk University, Kamenice 5, 625 00, Brno, Czech Republic. klan@sci.muni.cz., Weinstain R; School of Plant Sciences and Food Security, Faculty of Life Sciences, Tel-Aviv University, Tel-Aviv, 6997801, Israel. royweinstain@tauex.tau.ac.il.
Jazyk: angličtina
Zdroj: Nature communications [Nat Commun] 2022 Jun 24; Vol. 13 (1), pp. 3614. Date of Electronic Publication: 2022 Jun 24.
DOI: 10.1038/s41467-022-31288-2
Abstrakt: Photoremovable protecting groups (PPGs) represent one of the main contemporary implementations of photochemistry in diverse fields of research and practical applications. For the past half century, organic and metal-complex PPGs were considered mutually exclusive classes, each of which provided unique sets of physical and chemical properties thanks to their distinctive structures. Here, we introduce the meso-methylporphyrin group as a prototype hybrid-class PPG that unites traditionally exclusive elements of organic and metal-complex PPGs within a single structure. We show that the porphyrin scaffold allows extensive modularity by functional separation of the metal-binding chromophore and up to four sites of leaving group release. The insertion of metal ions can be used to tune their spectroscopic, photochemical, and biological properties. We provide a detailed description of the photoreaction mechanism studied by steady-state and transient absorption spectroscopies and quantum-chemical calculations. Our approach applied herein could facilitate access to a hitherto untapped chemical space of potential PPG scaffolds.
(© 2022. The Author(s).)
Databáze: MEDLINE
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