Rentmeister, Andrea and Arnold, Frances H. and Fasan, Rudi (2009) Chemo-enzymatic fluorination of unactivated organic compounds. Nature Chemical Biology, 5 (1). pp. 26-28. ISSN 1552-4450. PMCID PMC2713661. doi:10.1038/nchembio.128. https://resolver.caltech.edu/CaltechAUTHORS:RENncb09
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Abstract
Fluorination has gained an increasingly important role in drug discovery and development. Here we describe a versatile strategy that combines cytochrome P450–catalyzed oxygenation with deoxofluorination to achieve mono- and polyfluorination of nonreactive sites in a variety of organic scaffolds. This procedure was applied for the rapid identification of fluorinated drug derivatives with enhanced membrane permeability.
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| Additional Information: | © 2009 Nature Publishing Group. Received 11 August 2008; Accepted 27 October 2008; Published online 16 November 2008. We are grateful to M. Shahgholi for assistance with the LC-MS and HRMS analyses. This work was supported by US National Institutes of Health grant GM068664 and US Department of Agriculture grant 2006-35505-16660 to F.H.A. and by the Jacobs Institute (Caltech). A.R. acknowledges the Deutsche Forschungsgemeinschaft for financial support. Author contributions: R.F. and F.H.A. conceived the project; R.F. and A.R. performed the experiments; all authors discussed the results; R.F. wrote the paper with help and edits from F.H.A. and A.R. Declaration: R.F. and F.H.A. filed an international patent application (WO/2008/016709) entitled "Methods and systems for selective fluorination of organic molecules." Some of the P450 enzymes described in this work are available commercially from Codexis, Inc. F.H.A. is a minor shareholder of Codexis and serves on the Codexis Science Advisory Board. | ||||||||||||
| Group: | Jacobs Institute for Molecular Engineering for Medicine | ||||||||||||
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| Issue or Number: | 1 | ||||||||||||
| PubMed Central ID: | PMC2713661 | ||||||||||||
| DOI: | 10.1038/nchembio.128 | ||||||||||||
| Record Number: | CaltechAUTHORS:RENncb09 | ||||||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:RENncb09 | ||||||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||||||
| ID Code: | 13053 | ||||||||||||
| Collection: | CaltechAUTHORS | ||||||||||||
| Deposited By: | Archive Administrator | ||||||||||||
| Deposited On: | 17 Jan 2009 00:31 | ||||||||||||
| Last Modified: | 08 Nov 2021 22:35 |
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