Issue 2, 2014

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

Abstract

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.

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

Supplementary files

Article information

Article type
Edge Article
Submitted
09 Sep 2013
Accepted
01 Nov 2013
First published
04 Nov 2013

Chem. Sci., 2014,5, 598-601

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

Z. J. Wang, N. E. Peck, H. Renata and F. H. Arnold, Chem. Sci., 2014, 5, 598 DOI: 10.1039/C3SC52535J

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