z-logo
Premium
Photoinduced Electron Transfer‐Regulated Protein Labeling With a Coumarin‐Based Multifunctional Photocrosslinker
Author(s) -
Hotta Yusuke,
Kaneko Tsukasa,
Hayashi Ryuji,
Yamamoto Akito,
Morimoto Shota,
Chiba Junya,
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.201801673
Subject(s) - diazirine , chemistry , moiety , coumarin , photoinduced electron transfer , photochemistry , electron transfer , photodissociation , photoaffinity labeling , cleavage (geology) , ligand (biochemistry) , stereochemistry , combinatorial chemistry , organic chemistry , binding site , receptor , biochemistry , geotechnical engineering , fracture (geology) , engineering
We developed a novel diazirine‐based photolabeling agent having a (coumarin‐4‐yl)methyl ester scaffold, which exhibited multiple photochemical properties of crosslinking, fluorogenicity and cleavage. These properties can be kinetically regulated via photoinduced electron transfer between diazirine and coumarin moieties. The C−O bond of (coumarin‐4‐yl)methyl ester can be cleaved via photochemical excitation of coumarin moiety, that function has been initially quenched by the diazirine moiety. Upon diazirine photolysis with 365‐nm light, interacting protein was stably captured with photoactivatable ligand probe. Then, the unlocked cleavage function was activated with 313 nm light, and the reaction was accelerated in a weakly‐basic solution. The crosslinked protein could be selectively isolated with attachment of a small coumarin tag on the surface. This multi‐functional labeling agent has a great potential to facilitate LC‐MS/MS‐based protein identification.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here