This work was supported by a grant from Lhasa Limited.
Nitrogen Inversion Barriers Affect the N-Oxidation of Tertiary Alkylamines by Cytochromes P450†
Article first published online: 28 NOV 2012
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 52, Issue 3, pages 993–997, January 14, 2013
How to Cite
Rydberg, P., Jørgensen, M. S., Jacobsen, T. A., Jacobsen, A.-M., Madsen, K. G. and Olsen, L. (2013), Nitrogen Inversion Barriers Affect the N-Oxidation of Tertiary Alkylamines by Cytochromes P450 . Angew. Chem. Int. Ed., 52: 993–997. doi: 10.1002/anie.201206207
- Issue published online: 11 JAN 2013
- Article first published online: 28 NOV 2012
- Manuscript Revised: 7 NOV 2012
- Manuscript Received: 2 AUG 2012
- Lhasa Limited
- density functional calculations;
- N-inversion barrier;
Calculations: Cytochrome P450 enzymes facilitate a number of chemically different reactions. For example, amines can be either N-dealkylated or N-oxidized, but it is complex to rationalize which of these competing reactions occurs. It is shown that the barrier for inversion of the alkylamine nitrogen atom seems to be of vital importance for the amount of N-oxidized product formed relative to dealkylation and hydroxylation products.