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Comparative Analysis of the Reactivity of Diazirine‐Based Photoaffinity Probes toward a Carbohydrate‐Binding Protein
Author(s) -
Sakurai Kaori,
Yasui Tomoki,
Mizuno Sakae
Publication year - 2015
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201500116
Subject(s) - diazirine , chemistry , photoaffinity labeling , alkyl , reactivity (psychology) , stereochemistry , combinatorial chemistry , binding site , organic chemistry , biochemistry , medicine , alternative medicine , pathology
A set of lactose‐based photoaffinity probes bearing either alkyl diazirine or trifluoromethylphenyl diazirine (TPD) groups were designed and synthesized to directly compare their efficiency in photocrosslinking a carbohydrate‐binding protein. The crosslinking efficiency of the TPD probes was higher than the alkyl diazirine probes when reacted with a single binding protein. However, the alkyl diazirine probe with a small alkyne tag achieved more selective photoaffinity labeling of a binding protein in cell lysate than the corresponding TPD probe.