Site-specific bioconjugation has been used in diverse biological applications. For site-specific bioconjugation, various bioorthogonal chemistries have been developed. Certain bioorthogonal chemistries, such as strain-promoted azide-alkyne cycloaddition, exhibited relatively short reaction rates, hindering their applications in cellulo or in vivo. Therefore, recently, inverse electron-demand Diels-Alder cycloaddition (IEDDA) attracted much attention thanks to its fast reaction rates. So far several non-natural amino acids containing tetrazine functional group were developed for site-specific bioconjugation of proteins via IEDDA. However, in vivo applications of tetrazine-containing proteins were not yet extensively studied. We investigated the site-specific incorporation of a new variant of tetrazine containing non-natural amino acid into proteins and its bioconjugation via IEDDA. The new variant of tetrazine-containing non-natural amino acid showed a much faster reaction rate than previous versions of tetrazine-containing non-natural amino acid. Using the new variant of tetrazine-containing non-natural amino acid, time-controlled in vivo imaging of protein requiring a very fast bioconjugation reaction rate is under investigation.

Incorporation of non-natural amino acids containing a tetrazine functional group into proteins for fast site-specific bioconjugation

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.