Windle, CL, Berry, A and Nelson, A orcid.org/0000-0003-3886-363X (2017) Aldolase-Catalysed Stereoselective Synthesis of Fluorinated Small Molecules. Current Opinion in Chemical Biology, 37. pp. 33-38. ISSN 1367-5931
Abstract
The introduction of fluorine has been widely exploited to tune the biological functions of small molecules. Indeed, around 20% of leading drugs contain at least one fluorine atom. Yet, despite profound effects of fluorination on conformation, there is only a limited toolkit of reactions that enable stereoselective synthesis of fluorinated compounds. Aldolases are useful catalysts for the stereoselective synthesis of bioactive small molecules; however, despite fluoropyruvate being a viable nucleophile for some aldolases, the potential of aldolases to control the formation of fluorine-bearing stereocentres has largely been untapped. Very recently, it has been shown that aldolase-catalysed stereoselective carbonsingle bondcarbon bond formation with fluoropyruvate as nucleophile enable the synthesis of many α-fluoro β-hydroxy carboxyl derivatives. Furthermore, an understanding of the structural basis for the stereocontrol observed in these reactions is beginning to emerge. Here, we review the application of aldolase catalysis in the stereocontrolled synthesis of chiral fluorinated small molecules, and highlight likely areas for future developments.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2017 Elsevier Ltd. This is an author produced version of a paper published in Current Opinion in Chemical Biology. Uploaded in accordance with the publisher's self-archiving policy. |
Dates: |
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Institution: | The University of Leeds |
Academic Units: | The University of Leeds > Faculty of Engineering & Physical Sciences (Leeds) > School of Chemistry (Leeds) > Organic Chemistry (Leeds) |
Depositing User: | Symplectic Publications |
Date Deposited: | 05 Jan 2017 12:27 |
Last Modified: | 20 Jan 2018 01:38 |
Published Version: | https://doi.org/10.1016/j.cbpa.2016.12.029 |
Status: | Published |
Publisher: | Elsevier |
Identification Number: | 10.1016/j.cbpa.2016.12.029 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:110052 |