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Cytochrome P450-catalyzed insertion of carbenoids into N–H bonds

Wang, Z. Jane and Peck, Nicole E. and Renata, Hans and Arnold, Frances H. (2013) Cytochrome P450-catalyzed insertion of carbenoids into N–H bonds. Chemical Science, 5 (2). pp. 598-601. ISSN 2041-6520. PMCID PMC3906682. doi:10.1039/c3sc52535j.

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Expanding nature’s catalytic repertoire to include reactions important in synthetic chemistry will open new opportunities for ‘green’ chemistry and biosynthesis. We demonstrate the first enzyme-catalyzed insertion of carbenoids into N–H bonds. This type of bond disconnection, which has no counterpart in nature, can be mediated by variants of the cytochrome P450 from Bacillus megaterium. The N–H insertion reaction takes place in water, provides the desired products in 26–83% yield, forms the single addition product exclusively, and does not require slow addition of the diazo component.

Item Type:Article
Related URLs:
URLURL TypeDescription CentralArticle
Renata, Hans0000-0003-2468-2328
Arnold, Frances H.0000-0002-4027-364X
Additional Information:© 2014 The Royal Society of Chemistry. Received 09 Sep 2013; Accepted 01 Nov 2013; First published online 04 Nov 2013. A provisional patent based on the results presented here has been filed through Caltech. This research is funded by the Gordon and Betty Moore Foundation through Grant GBMF2809 to the Caltech Programmable Molecular Technology Initiative. Z. J. Wang was supported by a Ruth M. Kirschstein Fellowship from the National Institute of Health, award number F32EB015846-01. The authors thank Dr P. S. Coelho, Dr J. McIntosh, and Mr C. Farwell for useful discussions.
Funding AgencyGrant Number
Gordon and Betty Moore FoundationGBMF2809
NIH Predoctoral FellowshipF32EB015846-01
Issue or Number:2
PubMed Central ID:PMC3906682
Record Number:CaltechAUTHORS:20140130-083407487
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Official Citation:Wang, Z. J., Peck, N. E., Renata, H., & Arnold, F. H. (2014). Cytochrome P450-catalyzed insertion of carbenoids into N-H bonds. Chemical Science, 5(2), 598-601. doi: 10.1039/c3sc52535j
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:43567
Deposited By: Tony Diaz
Deposited On:14 Feb 2014 23:10
Last Modified:10 Nov 2021 16:39

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