incorporation of amino acids with long-chain terminal olefins into proteins
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2016
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Abstract
The increasing need for site-specific protein decorations that mimic natural posttranslational modifications requires access to a variety of noncanonical amino acids with moieties enabling bioorthogonal conjugation chemistry. Here we present the incorporation of long-chain olefinic amino acids into model proteins with rational variants of pyrrolysyl-tRNA synthetase (PylRS). Nε-heptenoyl lysine was incorporated for the first time using the known promiscuous variant PylRS(Y306A/Y384F), and Nε-pentenoyl lysine was incorporated in significant yields with the novel variant PylRS(C348A/Y384F). This is the only example of rational modification at position C348 to enlarge the enzyme’s binding pocket. Furthermore, we demonstrate the feasibility of our chosen amino acids in the thiol-ene conjugation reaction with a thiolated polysaccharide.
| Reference Key |
exner2016moleculesincorporation
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|---|---|
| Authors | ;Matthias P. Exner;Sebastian Köhling;Julie Rivollier;Sandrine Gosling;Puneet Srivastava;Zheni I. Palyancheva;Piet Herdewijn;Marie-Pierre Heck;Jörg Rademann;Nediljko Budisa |
| Journal | Journal of ethnopharmacology |
| Year | 2016 |
| DOI |
10.3390/molecules21030287
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| URL | |
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