Several bioorthogonal chemical reactions have been explored for the selective modification of proteins, including the coupling of alkoxyamines and hydrazides to ketones or aldehydes, the Staudinger ligation of azides to modified phosphines, and click reactions between azides and alkynes. Recently, alkene moieties have also been exploited as uniquely reactive chemical handles. Examples include, the photoaddition of a diaryl tetrazole to alkenes; a Diels-Alder reaction between tetrazines and trans-cyclooctenes; the cross-metathesis of olefins with allyl thioether modified proteins; the copolymerization of alkene-containing proteins and acrylamide; and the coupling of two alkene-containing residues in peptides, resulting in improved stability and pharmacological properties.
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