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Tag‐Convertible Photocrosslinker with Click‐On/Off N ‐Acylsulfonamide Linkage for Protein Identification
Author(s) -
Hayashi Ryuji,
Morimoto Shota,
Tomohiro Takenori
Publication year - 2019
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201900859
Subject(s) - moiety , linker , bioorthogonal chemistry , chemistry , click chemistry , derivative (finance) , combinatorial chemistry , coumarin , photoaffinity labeling , identification (biology) , linkage (software) , stereochemistry , biochemistry , binding site , biology , organic chemistry , computer science , botany , gene , financial economics , economics , operating system
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.