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Comparison of the Reactivity of Carbohydrate Photoaffinity Probes with Different Photoreactive Groups
Author(s) -
Sakurai Kaori,
Ozawa Shimpei,
Yamada Rika,
Yasui Tomoki,
Mizuno Sakae
Publication year - 2014
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201402051
Subject(s) - diazirine , photoaffinity labeling , chemistry , reactivity (psychology) , combinatorial chemistry , ligand (biochemistry) , selectivity , lysis , yield (engineering) , stereochemistry , binding site , biochemistry , receptor , medicine , materials science , alternative medicine , pathology , metallurgy , catalysis
A judicious choice of photoreactive group is critical in successful photoaffinity labeling studies of small molecule–protein interactions. A set of carbohydrate‐based photoaffinity probes was prepared to compare the effects of three major photoreactive groups on the efficiency and selectivity of crosslinking a binding protein with low affinity. We showed that, despite the low crosslinking yield, the diazirine probe displayed the high ligand‐dependent reactivity consistent with the ideal mechanism of photoaffinity labeling. Moreover, we demonstrated that, among the three photoreactive groups, only the diazirine probe achieved highly selective crosslinking of a low‐affinity binding protein in cell lysate.