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Published August 26, 2013 | Version Accepted Version
Journal Article Open

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

Creators

  • 1. ROR icon California Institute of Technology
  • 2. ROR icon University of Chicago

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.

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.

Attached Files

Accepted Version - nihms565524.pdf

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Additional details

Identifiers

PMCID
PMC3988694
Eprint ID
41647
DOI
10.1002/anie.201304401
Resolver ID
CaltechAUTHORS:20131003-083816907

Funding

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

Dates

Created
2013-10-03
Created from EPrint's datestamp field
Updated
2021-11-10
Created from EPrint's last_modified field

Caltech Custom Metadata

Caltech groups
Jacobs Institute for Molecular Engineering for Medicine