Metalloenzymes Catalyze Nitrene Transfer Reactions

  • Author: ChemBioChem
  • Published Date: 16 April 2020
  • Source / Publisher: ChemBioChem/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
thumbnail image: Metalloenzymes Catalyze Nitrene Transfer Reactions

Related Societies

Direct C–H aminations via nitrene transfer provide a useful synthetic strategy for the preparation of amines. These reactions are traditionally performed using transition-metal catalysts. However, "nitrene transferase" enzymes have recently emerged as an alternative to promote these transformations via mild, cost-effective, and environmentally friendly biocatalytic processes.


Ignacio Carrera, Universidad de la República, Montevideo, Uruguay, Rudi Fasan, University of Rochester, NY, USA, and colleagues have tested a range of functionally and structurally different non‐heme iron‐dependent oxidases for their C−H amination activity. They found that several of these enzymes, including Rieske dioxygenases and α‐ketoglutarate‐dependent dioxygenases and halogenases, can function as C–H aminases via nitrene transfer chemistry.


The most promising catalyst, naphthalene dioxygenase (NDO), showed high conversion and chemoselectivity in a gram-scale biotransformation of a sulfonyl azide substrate into the corresponding C-H amination product. This enzyme is reasonably oxygen tolerant, in contrast to previously reported hemoprotein-based biocatalysts, which require strictly anaerobic conditions. This work could be a basis for further studies of transformations using non-heme iron-dependent enzymes.


 

 

 

 

 

Article Views: 1130

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

Bookmark and Share

If you would like to reuse any content, in print or online, from ChemistryViews.org, please contact us first for permission. more


CONNECT:

ChemistryViews.org on Facebook

ChemistryViews.org on Twitter ChemistryViews.org on YouTube ChemistryViews.org on LinkedIn Sign up for our free newsletter


Magazine of Chemistry Europe (16 European Chemical Societies)published by Wiley-VCH