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Bioconjugation is a chemical technique used to couple two molecules together, at least one of which is a biomolecule, such as a carbohydrate, nucleic acid, or protein. Proteins are especially diverse biomolecules due to the variety of amino acids available and are thus important substrates in bioconjugation reactions.<br /><br />The nsAA para-azido-phenylalanine (pAzF) can encode a biorthogonal chemical moiety that facilitates "click" reactions to attach diverse chemical groups for protein functionalization. However, the azide moiety is unstable in physiological conditions and is reduced to para-amino-phenylalanine (pAF).