A novel bioconjugation reaction is reported in which anilines are photochemically coupled to azidophenols at pH 6 in aqueous solution. This new technique reaches high conversion in 5 minutes with 302 nm irradiation, and exhibits the same chemoselectivity, speed, and high conversion that has been characteristic of previous oxidative coupling reactions. By incorporating a photochemical trigger, the prior need for added strong oxidants (such as sodium periodate) can be avoided. Additional small-molecule studies revealed a minor byproduct formation pathway that can be terminated with addition of mild oxidants, if desired. The bimolecular compatibility of this strategy was confirmed by reacting aniline-containing protein substrates with small molecules, polymers, and other biomolecules.

Rapid and chemoselective photoactivated bioconjugation of anilines with azidophenols

245th National Meeting (2013)

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