Nitrogen inversion barriers affect the N-oxidation of tertiary alkylamines by cytochromes P450

TY - JOUR

T1 - Nitrogen inversion barriers affect the N-oxidation of tertiary alkylamines by cytochromes P450

AU - Rydberg, Patrik

AU - Jørgensen, Martin S.

AU - Jacobsen, T.A.

AU - Jacobsen, A.-M.

AU - Madsen, Kim G.

AU - Olsen, L.

PY - 2013/1/14

Y1 - 2013/1/14

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=84872328870&partnerID=8YFLogxK

U2 - 10.1002/anie.201206207

DO - 10.1002/anie.201206207

M3 - Journal article

C2 - 23192954

AN - SCOPUS:84872328870

SN - 1433-7851

VL - 52

SP - 993

EP - 997

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 3

ER -