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Enantioselective Intramolecular C-H Amination Catalyzed by Engineered Cytochrome P450 Enzymes In Vitro and In Vivo

McIntosh, John A. and Coelho, Pedro S. and Farwell, Christopher C. and Wang, Z. Jane and Lewis, Jared C. and Brown, Tristan R. and Arnold, Frances H. (2013) Enantioselective Intramolecular C-H Amination Catalyzed by Engineered Cytochrome P450 Enzymes In Vitro and In Vivo. Angewandte Chemie International Edition, 52 (35). pp. 9309-9312. ISSN 1433-7851. PMCID PMC3988694. https://resolver.caltech.edu/CaltechAUTHORS:20131003-083816907

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Abstract

Nitrogen activation: Though P450 enzymes are masters of oxygen activation and insertion into C-H bonds, their ability to use nitrogen for the same purpose has so far not been explored. Engineered variants of cytochrome P450_(BM3) have now been found to catalyze intramolecular C-H aminations in azide substrates. Mutations to two highly conserved residues significantly increased this activity.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/anie.201304401 DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/anie.201304401/abstractPublisherArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3988694PubMed CentralArticle
ORCID:
AuthorORCID
McIntosh, John A.0000-0002-9487-490X
Arnold, Frances H.0000-0002-4027-364X
Additional Information:© 2013 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Received: May 22, 2013; Revised: June 12, 2013; Published online: July 24, 2013. We thank S. Virgil and the 3CS catalysis center at Caltech for assistance with HPLC and LC–MS analyses, and D. Montgomery, Y. Liu, N. Peck, K. Rabe, R. Lauchli, and D. VanderVelde for helpful discussions. This work was supported by the Department of the Navy, Office of Naval Research (grant N00014-11-1-0205), and by the Jacobs Institute for Molecular Engineering for Medicine at Caltech. J.A.M. and Z.J.W. are supported by Ruth L. Kirschstein National Research Service Awards (F32GM101792) and (F32EB015846). C.C.F. is supported by an NSF Graduate Research Fellowship.
Group:Jacobs Institute for Molecular Engineering for Medicine
Funders:
Funding AgencyGrant Number
Office of Naval Research (ONR)N00014-11-1-0205
Jacobs Institute for Molecular Engineering for MedicineUNSPECIFIED
NIH Predoctoral FellowshipF32GM101792
NIH Predoctoral FellowshipF32EB015846
NSF Graduate Research FellowshipUNSPECIFIED
Subject Keywords:C-H activation; cytochromes; enzyme catalysis; protein engineering; synthetic biology
Issue or Number:35
PubMed Central ID:PMC3988694
Record Number:CaltechAUTHORS:20131003-083816907
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20131003-083816907
Official Citation:McIntosh, J. A., Coelho, P. S., Farwell, C. C., Wang, Z. J., Lewis, J. C., Brown, T. R. and Arnold, F. H. (2013), Enantioselective Intramolecular C[BOND]H Amination Catalyzed by Engineered Cytochrome P450 Enzymes In Vitro and In Vivo . Angew. Chem. Int. Ed., 52: 9309–9312. doi: 10.1002/anie.201304401
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:41647
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:03 Oct 2013 16:26
Last Modified:14 Oct 2019 17:37

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