We designed and synthesised peptides conjugated with proline linkers and ruthenium photocatalysts. These peptides were used as substrates to evaluate the photocatalyst-proximity dependences of candidates for tyrosine labelling reagents. The 1-methyl-4-aryl-urazole (MAUra) structure was found to be a novel tyrosyl radical trapping agent to label tyrosine residues effectively under the conditions where the ruthenium photocatalyst and tyrosine were in close proximity. Using a ruthenium photocatalyst conjugated to a carbonic anhydrase ligand, the target protein in a complex protein mixture was labelled with remarkable target selectivity by azide- or desthiobiotin-conjugated MAUra derivatives.
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