Enantioselective, intermolecular benzylic C-H amination catalysed by an engineered iron-haem enzyme

Author: Prier, C.K.; Zhang, R.K.; Buller, A.R.; Brinkmann-Chen, S.; Arnold, F.H.

Description: C-H bonds are ubiquitous structural units of organic molecules. Although these bonds are generally considered to be chemically inert, the recent emergence of methods for C-H functionalization promises to transform the way synthetic chemistry is performed. The intermolecular amination of C-H bonds represents a particularly desirable and challenging transformation for which no efficient, highly selective, and renewable catalysts exist. Here we report the directed evolution of an iron-containing enzymatic catalyst-based on a cytochrome P450 monooxygenase-for the highly enantioselective intermolecular amination of benzylic C-H bonds. The biocatalyst is capable of up to 1,300 turnovers, exhibits excellent enantioselectivities, and provides access to valuable benzylic amines. Iron complexes are generally poor catalysts for C-H amination: in this catalyst, the enzyme’s protein framework confers activity on an otherwise unreactive iron-haem cofactor.

Subject headings:

Publication year: 2017

Journal or book title: Nature Chemistry

Volume: 9

Issue: 7

Pages: 629-634

Find the full text : https://www.nature.com/articles/nchem.2783

Find more like this one (cited by): https://scholar.google.com/scholar?cites=12450939709222528676&as_sdt=1000005&sciodt=0,16&hl=en

Type: Journal Article

Serial number: 2115