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Extending the biocatalytic scope of regiocomplementary flavin-dependent halogenase enzymes

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Shepherd, Sarah A., Karthikeyan, Chinnan, Latham, Jonathan, Struck, Anna-Winona, Thompson, Mark L., Menon, Binuraj R. K., Styles, Matthew Q., Levy, Colin, Leys, David and Micklefield, Jason (2015) Extending the biocatalytic scope of regiocomplementary flavin-dependent halogenase enzymes. Chemical Science, 6 (6). pp. 3454-3460. doi:10.1039/C5SC00913H

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Official URL: http://dx.doi.org/10.1039/C5SC00913H

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Abstract

Flavin-dependent halogenases are potentially valuable biocatalysts for the regioselective halogenation of aromatic compounds. These enzymes, utilising benign inorganic halides, offer potential advantages over traditional non-enzymatic halogenation chemistry that often lacks regiocontrol and requires deleterious reagents. Here we extend the biocatalytic repertoire of the tryptophan halogenases, demonstrating how these enzymes can halogenate a range of alternative aryl substrates. Using structure guided mutagenesis we also show that it is possible to alter the regioselectivity as well as increase the activity of the halogenases with non-native substrates including anthranilic acid; an important intermediate in the synthesis and biosynthesis of pharmaceuticals and other valuable products.

Item Type: Journal Article
Divisions: Faculty of Science, Engineering and Medicine > Science > Life Sciences (2010- )
Journal or Publication Title: Chemical Science
Publisher: Royal Society of Chemistry
ISSN: 2041-6520
Official Date: 2015
Dates:
DateEvent
2015Published
Volume: 6
Number: 6
Page Range: pp. 3454-3460
DOI: 10.1039/C5SC00913H
Status: Peer Reviewed
Publication Status: Published
Access rights to Published version: Restricted or Subscription Access

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