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. doi:10.1002/anie.201304401. 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:

URL	URL Type	Description
http://dx.doi.org/10.1002/anie.201304401	DOI	Article
http://onlinelibrary.wiley.com/doi/10.1002/anie.201304401/abstract	Publisher	Article
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3988694	PubMed Central	Article

ORCID:

Author	ORCID
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 Agency	Grant Number
Office of Naval Research (ONR)	N00014-11-1-0205
Jacobs Institute for Molecular Engineering for Medicine	UNSPECIFIED
NIH Predoctoral Fellowship	F32GM101792
NIH Predoctoral Fellowship	F32EB015846
NSF Graduate Research Fellowship	UNSPECIFIED

Subject Keywords:

C-H activation; cytochromes; enzyme catalysis; protein engineering; synthetic biology

Issue or Number:

PubMed Central ID:

PMC3988694

DOI:

10.1002/anie.201304401

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

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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:

10 Nov 2021 04:32

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