Caffeine Biodegradation by Cytochrome P450 1A2. What Determines the Product Distributions?

Abstract: Caffeine is a natural compound found in plant seeds that after consumption by humans effects the central nervous system as well as the cardiovascular system. In general, the cytochrome P450 enzymes in the liver are involved in the biodegradation of caffeine, which gives paraxanthine, theobromine and theophylline products. There has been debate for many years why multiple products are obtained and how their distributions are determined. To this end we performed a high‐level computational study using a combination of molecular dynamics and quantum mechanical approaches. A series of quantum chemical cluster models on the mechanism of caffeine activation by P450 model complexes give hydrogen atom abstraction barriers that predicts the correct ordering and statistical distribution of products. Our studies highlight that second‐coordination sphere effects and thermochemical properties of the substrate determine the product distributions.

Location
Deutsche Nationalbibliothek Frankfurt am Main
Extent
Online-Ressource
Language
Englisch

Bibliographic citation
Caffeine Biodegradation by Cytochrome P450 1A2. What Determines the Product Distributions? ; day:25 ; month:04 ; year:2023 ; extent:11
Chemistry - a European journal ; (25.04.2023) (gesamt 11)

Creator
Mokkawes, Thirakorn
de Visser, Sam P.

DOI
10.1002/chem.202203875
URN
urn:nbn:de:101:1-2023042515580829298599
Rights
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
Last update
14.08.2025, 10:51 AM CEST

Data provider

This object is provided by:
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.

Associated

  • Mokkawes, Thirakorn
  • de Visser, Sam P.

Other Objects (12)