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Molecules 2016, 21(3), 287; doi:10.3390/molecules21030287

Incorporation of Amino Acids with Long-Chain Terminal Olefins into Proteins

1
Institute of Chemistry, Technische Universität Berlin, Mueller-Breslau-Strasse 10, 10623 Berlin, Germany
2
Institute of Pharmacy, Freie Universität Berlin, Königin-Luise-Str. 2+4, 14195 Berlin, Germany
3
Service de Chimie Bioorganique et de Marquage, iBiTecS, CEA, 91191 Gif-sur-Yvette, France
4
Medicinal Chemistry, Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, 3000 Leuven, Belgium
*
Author to whom correspondence should be addressed.
Academic Editors: Jose M. Palomo and Chris Frost
Received: 16 January 2016 / Revised: 23 February 2016 / Accepted: 25 February 2016 / Published: 29 February 2016
(This article belongs to the Special Issue Biomolecules Modification)
View Full-Text   |   Download PDF [1535 KB, uploaded 29 February 2016]   |  

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. View Full-Text
Keywords: stop codon suppression; protein decoration; noncanonical amino acid; pyrrolysyl-tRNA synthetase; thiol-ene coupling; metathesis stop codon suppression; protein decoration; noncanonical amino acid; pyrrolysyl-tRNA synthetase; thiol-ene coupling; metathesis
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

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.

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