Incorporation of Amino Acids with Long-Chain Terminal Olefins into Proteins
AbstractThe 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. View Full-Text
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Exner, M.P.; Köhling, S.; Rivollier, J.; Gosling, S.; Srivastava, P.; Palyancheva, Z.I.; Herdewijn, P.; Heck, M.-P.; Rademann, J.; Budisa, N. Incorporation of Amino Acids with Long-Chain Terminal Olefins into Proteins. Molecules 2016, 21, 287.
Exner MP, Köhling S, Rivollier J, Gosling S, Srivastava P, Palyancheva ZI, Herdewijn P, Heck M-P, Rademann J, Budisa N. Incorporation of Amino Acids with Long-Chain Terminal Olefins into Proteins. Molecules. 2016; 21(3):287.Chicago/Turabian Style
Exner, Matthias P.; Köhling, Sebastian; Rivollier, Julie; Gosling, Sandrine; Srivastava, Puneet; Palyancheva, Zheni I.; Herdewijn, Piet; Heck, Marie-Pierre; Rademann, Jörg; Budisa, Nediljko. 2016. "Incorporation of Amino Acids with Long-Chain Terminal Olefins into Proteins." Molecules 21, no. 3: 287.
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