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- Title
Incorporation of Amino Acids with Long-Chain Terminal Olefins into Proteins.
- Authors
Exner, Matthias P.; Köhling, Sebastian; Rivollier, Julie; Gosling, Sandrine; Srivastava, Puneet; Palyancheva, Zheni I.; Herdewijn, Piet; Heck, Marie-Pierre; Rademann, Jörg; Budisa, Nediljko
- 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). Ne-heptenoyl lysine was incorporated for the first time using the known promiscuous variant PylRS(Y306A/Y384F), and Ne-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.
- Subjects
AMINO acids; AMINO compounds; ALKENES; ACIDOLYSIS; CHEMICAL reactions
- Publication
Molecules, 2016, Vol 21, Issue 3, p287
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules21030287