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Issue 36, 2012
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Organic fluorine as a polypeptide building element: in vivo expression of fluorinated peptides, proteins and proteomes

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Abstract

Traditionally, the biological fluorination of complex biological systems like proteins is achieved through substitution of canonical amino acids or addition of fluorinated amino acids in the context of the standard genetic code. Ribosomal translation of monofluorinated amino acids into proteins often yields structures with minimal local changes in the interior but, on the same time, results in large global effects on characteristic features of the biopolymers (such as dramatically changed activity profile or folding stability). This is due to the novel and unique local interactions delivered by fluorine atoms such as (i) increase in the covalent radii (ii) changed polarities; (iii) changed hydrogen bond acceptor ability; (iv) altered water solubility as well as water ↔ organic solvent energy transfer. On the other hand, the biological incorporation of tri- or global fluorinated amino acids (such as trifluoroleucine, triflurovaline, and their hexafluoro counterparts, fluoromethionine and trifluoronorleucine etc.) represents still a challenge, as the natural structural scaffolds are optimized for hydrocarbon during evolution but not for fluorocarbon cores. Future work will be focused on the re-design of existing or de novo design of novel protein scaffolds capable of accommodating such building blocks into functional biologically active proteins and proteomes in the context of the viable cells.

Graphical abstract: Organic fluorine as a polypeptide building element: in vivo expression of fluorinated peptides, proteins and proteomes

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Article information


Submitted
15 Nov 2011
Accepted
09 Jul 2012
First published
13 Jul 2012

Org. Biomol. Chem., 2012,10, 7241-7261
Article type
Emerging Area

Organic fluorine as a polypeptide building element: in vivo expression of fluorinated peptides, proteins and proteomes

L. Merkel and N. Budisa, Org. Biomol. Chem., 2012, 10, 7241
DOI: 10.1039/C2OB06922A

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