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• W2314090070 abstract "Cytochrome P450 enzymes (CYPs) metabolize alkyl- and arylamines, generating several different products. For the primary and secondary amines, some of these reactions result in hydroxylated amines, which may be toxic. Thus, when designing new drugs containing amine groups, it is important to be able to predict if a given compound will be a substrate for CYPs, in order to avoid toxic metabolites, and hence to understand the mechanism that is utilized by CYPs. Two possible mechanisms, for the N-hydroxylation of primary and secondary amines mediated by CYPs, are studied by density functional theory (DFT) for four different amines (aniline, N-methylaniline, propan-2-amine, and dimethylamine). The hydrogen abstraction and rebound mechanism is found to be preferred over a direct oxygen transfer mechanism for all four amines. However, in contrast to the same mechanism for the hydroxylation of aliphatic carbon atoms, the rebound step is shown to be rate-limiting in most cases." @default.
• W2314090070 created "2016-06-24" @default.
• W2314090070 creator A5002139604 @default.
• W2314090070 creator A5006357853 @default.
• W2314090070 creator A5029979966 @default.
• W2314090070 date "2015-02-12" @default.
• W2314090070 modified "2023-10-13" @default.
• W2314090070 title "Mechanism of the N-Hydroxylation of Primary and Secondary Amines by Cytochrome P450" @default.
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• W2314090070 doi "https://doi.org/10.1021/tx500371a" @default.
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• W2314090070 hasPublicationYear "2015" @default.
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