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Chemo-enzymatic fluorination of unactivated organic compounds

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. 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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1038/nchembio.128DOIArticle
https://rdcu.be/4SxKPublisherFree ReadCube access
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2713661PubMed CentralArticle
ORCID:
AuthorORCID
Rentmeister, Andrea0000-0002-3107-4147
Arnold, Frances H.0000-0002-4027-364X
Fasan, Rudi0000-0003-4636-9578
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
Funders:
Funding AgencyGrant Number
NIHGM068664
Department of Agriculture (USDA)2006-35505-16660
Jacobs Institute of Molecular Engineering for MedicineUNSPECIFIED
Deutsche Forschungsgemeinschaft (DFG)UNSPECIFIED
Issue or Number:1
PubMed Central ID:PMC2713661
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:17 Dec 2019 00:29

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