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Nitrogen Inversion Barriers Affect the N‐Oxidation of Tertiary Alkylamines by Cytochromes P450

2012; Wiley; Volume: 52; Issue: 3 Linguagem: Inglês

10.1002/anie.201206207

1521-3773

Patrik Rydberg, Martin S. Jørgensen, Thomas A. Jacobsen, Anne‐Marie Jacobsen, K. Madsen, Lars Olsen,

Cancer, Hypoxia, and Metabolism

Angewandte Chemie International EditionVolume 52, Issue 3 p. 993-997 Communication Nitrogen Inversion Barriers Affect the N-Oxidation of Tertiary Alkylamines by Cytochromes P450† Dr. Patrik Rydberg, Dr. Patrik Rydberg Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, Universitetsparken 2, 2100 Copenhagen (Denmark)Search for more papers by this authorMartin S. Jørgensen, Martin S. Jørgensen Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, Universitetsparken 2, 2100 Copenhagen (Denmark)Search for more papers by this authorDr. Thomas A. Jacobsen, Dr. Thomas A. Jacobsen Aniona, Pederstrupvej 93, 2750 Ballerup (Denmark)Search for more papers by this authorDr. Anne-Marie Jacobsen, Dr. Anne-Marie Jacobsen Department of Drug Metabolism, H. Lundbeck A/S, Ottiliavej 9, 2500 Valby (Denmark)Search for more papers by this authorDr. Kim G. Madsen, Dr. Kim G. Madsen ADME Department, Novo Nordisk A/S, Novo Nordisk Park, 2760 Måløv (Denmark)Search for more papers by this authorDr. Lars Olsen, Corresponding Author Dr. Lars Olsen lo@sund.ku.dk Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, Universitetsparken 2, 2100 Copenhagen (Denmark)Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, Universitetsparken 2, 2100 Copenhagen (Denmark)Search for more papers by this author Dr. Patrik Rydberg, Dr. Patrik Rydberg Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, Universitetsparken 2, 2100 Copenhagen (Denmark)Search for more papers by this authorMartin S. Jørgensen, Martin S. Jørgensen Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, Universitetsparken 2, 2100 Copenhagen (Denmark)Search for more papers by this authorDr. Thomas A. Jacobsen, Dr. Thomas A. Jacobsen Aniona, Pederstrupvej 93, 2750 Ballerup (Denmark)Search for more papers by this authorDr. Anne-Marie Jacobsen, Dr. Anne-Marie Jacobsen Department of Drug Metabolism, H. Lundbeck A/S, Ottiliavej 9, 2500 Valby (Denmark)Search for more papers by this authorDr. Kim G. Madsen, Dr. Kim G. Madsen ADME Department, Novo Nordisk A/S, Novo Nordisk Park, 2760 Måløv (Denmark)Search for more papers by this authorDr. Lars Olsen, Corresponding Author Dr. Lars Olsen lo@sund.ku.dk Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, Universitetsparken 2, 2100 Copenhagen (Denmark)Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, Universitetsparken 2, 2100 Copenhagen (Denmark)Search for more papers by this author First published: 28 November 2012 https://doi.org/10.1002/anie.201206207Citations: 20 † This work was supported by a grant from Lhasa Limited. Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat Abstract 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. Citing Literature Supporting Information Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Filename Description anie_201206207_sm_miscellaneous_information.pdf553.5 KB miscellaneous_information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. Volume52, Issue3January 14, 2013Pages 993-997 RelatedInformation