Electrochemical Tryptophan-Selective Bioconjugation
2019
Bioconjugation
reactions are a fundamental synthetic method for generating artificial peptides
and proteins. Despite the potentially superior properties of bioconjugates at
hydrophobic amino acid residues compared with those at hydrophilic amino acids,
methods to target hydrophobic amino acids with moderate reactivity under mild
and metal-free conditions are limited. Here we report the first
electrochemically-promoted tryptophan (Trp)-selective bioconjugation of
peptides and proteins in neutral aqueous media. The unique electrochemical
cooperation of two radicals, keto-ABNO and 4-oxo-TEMPO, was critical to
suppress both anodic overoxidation of the products and cross reactivity.
Systematic cyclic voltammetry analysis suggested that these two radicals,
containing similar redox potentials but contrasting steric demands, had
distinct electrochemical roles (reactant and electrochemical mediator). This new
protocol will be an important advance toward clean and scalable syntheses of
chemically modified biologics.
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