Abstract
Singlet oxygen is a short half-life cytotoxic agent which can be generated by chemical and photochemical methods. In order to make use of its antibacterial action at a selected location, it is desirable to have singlet oxygen in a relatively stable, “caged” structure, in the form of an endoperoxide. Here, the trimethylsilyl (TMS) group supplies the steric bulk, inhibiting the cycloreversion reaction to produce very little singlet oxygen under ambient conditions. However, when fluoride ions are added as tetrabutylammonium fluoride, very rapid removal of the TMS group takes place, followed by the unhindered cycloreversion, releasing singlet oxygen much faster. The bactericidal action on surfaces was demonstrated using E. coli, and imaged under fluorescence microscopy. Considering the issues related to emergence of antibiotic resistant bacterial strains, “on demand singlet oxygen” appears to be an exciting alternative.
Highlights
Among the reactive oxygen species (ROS), singlet oxygen is the most reactive and short-lived.[1]
We propose that the chemical generation of singlet oxygen could extend the applicability of singlet oxygen as an effective antibacterial agent
We synthesized its structural isomer where the steric hindrance is on C-2, but steric block on the other side of the bridgehead substitution, may offer additional advantages in deprotection rates and/or stability of the initial endoperoxide
Summary
Among the reactive oxygen species (ROS), singlet oxygen is the most reactive and short-lived.[1]. The singlet aState Key Laboratory of Fine Chemicals, Dalian University of Technology, 2 Linggong Road, 116024, Dalian, China. The crude product was puri ed by column chromatography (15%, EtOAc in n-hexane) to afford 2-(2-bromophenyl)-N-methoxy-Nmethylacetamide (2) as a colorless oil.
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