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Incorporation of Amino Acids with Long-Chain Terminal Olefins into Proteins
Citation key 136.2016.exner
Author Exner, M. P. and Köhling, S. and Rivollier, J. and Gosling, S. and Srivastava, P. and Palyancheva, Z. I. and Herdewijn, P. and Heck, M-P. and Rademann, J. and Budisa, N.
Pages 287
Year 2016
DOI 10.3390/molecules21030287
Journal Molecules
Volume 21
Number 3
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.
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