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Molecules
Volume 21
Issue 3
10.3390/molecules21030287
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Article

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

by
Matthias P. Exner
1,
Sebastian Köhling
2,
Julie Rivollier
3,
Sandrine Gosling
3,
Puneet Srivastava
4,
Zheni I. Palyancheva
1,
Piet Herdewijn
4,
Marie-Pierre Heck
3,
Jörg Rademann
2 and
Nediljko Budisa
1,*
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
Molecules 2016, 21(3), 287; https://doi.org/10.3390/molecules21030287
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)
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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. 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

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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. https://doi.org/10.3390/molecules21030287

AMA Style

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. https://doi.org/10.3390/molecules21030287

Chicago/Turabian Style

Exner, Matthias P., Sebastian Köhling, Julie Rivollier, Sandrine Gosling, Puneet Srivastava, Zheni I. Palyancheva, Piet Herdewijn, Marie-Pierre Heck, Jörg Rademann, and Nediljko Budisa. 2016. "Incorporation of Amino Acids with Long-Chain Terminal Olefins into Proteins" Molecules 21, no. 3: 287. https://doi.org/10.3390/molecules21030287

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