The uniquely diverse structures and functions of biomolecules offer many exciting opportunities for creating new materials with advanced properties. Using only a limited set of side chains and auxiliary groups, they have evolved unparalleled abilities to accelerate chemical transformations, facilitate the delivery of genetic cargo to targeted cells, bind specific analytes in complex mixtures, transduce energy, and generate elaborate three-dimensional structures through self-assembly. Over the years, our lab has sought to incorporate these capabilities into new materials for use in diagnostic imaging, solar energy collection, and water purification. To do this, however, we also needed to develop new chemical strategies that can attach synthetic molecules and polymers to single locations on a wide range of biomolecules. This presentation will focus on the development of a powerful set of oxidative coupling reactions that involve o-quinone and o-iminoquinone intermediates. These species can modify proteins with very high chemoselectivity and efficiency, and have been adapted for use in a large number of experimental contexts. Newer versions of these reactions involve the use of oxidative enzymes that can generate o-quinone intermediates from simple phenols using molecular oxygen as the stoichiometric oxidant. The chemical development of these reactions will be presented, along with several examples of new protein bioconjugates that have been prepared through their use.

Award Address (Arthur C. Cope Mid-Career Scholars Award sponsored by the Arthur C. Cope Fund). Versatile oxidative coupling reactions for site-selective protein modification

2019 Fall National Meeting

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