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Nitrogen Inversion Barriers Affect the N‐Oxidation of Tertiary Alkylamines by Cytochromes P450
Author(s) -
Rydberg Patrik,
Jørgensen Martin S.,
Jacobsen Thomas A.,
Jacobsen AnneMarie,
Madsen Kim G.,
Olsen Lars
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201206207
Subject(s) - hydroxylation , chemistry , cytochrome p450 , nitrogen , nitrogen atom , alkylation , enzyme , stereochemistry , organic chemistry , catalysis , alkyl
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.