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Tag-Convertible Photocrosslinker with Click-On/Off N-Acylsulfonamide Linkage for Protein Identification
Ryuji Hayashi1, Shota Morimoto1,2, Takenori Tomohiro1
1Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama, 930-0194, Japan.
Abstract:
The N-acylsulfonamide group, known as a safety-catch linker, has been applied to photoaffinity labeling (PAL) using a cinnamate-type photocrosslinker to improve the efficiency of PAL-based target identification. A bioorthogonal sulfo-click reaction was used to stably link a photocrosslinker unit with N-acylsulfonamide linkage to produce a photoactivatable probe without any protection. In addition, the crosslinked protein was selectively isolated with a small cinnamate tag via linkage disruption upon N-alkylation. Furthermore, the tag moiety was photochemically converted to a stable coumarin derivative by losing a water molecule, which is a useful property in MS-based identification.
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