Advanced

Sulfoxide, sulfur, and nitrogen oxidation and dealkylation by cytochrome P450

Rydberg, Patrik ; Ryde, Ulf LU and Olsen, Lars (2008) In Journal of Chemical Theory and Computation 4(8). p.1369-1377
Abstract
The oxidation and dealkylation of dimethylsulfoxide (DMSO), dimethylsulfide (DMS), and trimethylamine (TMA) by cytochrome P450 has been studied with density functional theory calculations. The results show that the oxidation reactions always occur on the doublet spin surface, whereas dealkylations can take place for both the doublet and quartet spin states. Moreover, DMS is more reactive than DMSO, and S-oxidation is more favorable than S-dealkylation, whereas N-dealkylation is more favorable than N-oxidation. This is in perfect agreement with experimental results, showing that density functional activation energies are reliable and comparable for widely different reactions with cytochrome P450.
Please use this url to cite or link to this publication:
author
; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Chemical Theory and Computation
volume
4
issue
8
pages
1369 - 1377
publisher
The American Chemical Society (ACS)
external identifiers
  • wos:000258400600022
  • scopus:58149157800
  • pmid:26631712
ISSN
1549-9618
DOI
10.1021/ct800101v
language
English
LU publication?
yes
additional info
The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Theoretical Chemistry (S) (011001039)
id
4ab432cc-1ccc-46ae-8756-c907340915ea (old id 1252833)
date added to LUP
2016-04-01 11:38:46
date last changed
2020-12-08 05:08:17
@article{4ab432cc-1ccc-46ae-8756-c907340915ea,
  abstract     = {The oxidation and dealkylation of dimethylsulfoxide (DMSO), dimethylsulfide (DMS), and trimethylamine (TMA) by cytochrome P450 has been studied with density functional theory calculations. The results show that the oxidation reactions always occur on the doublet spin surface, whereas dealkylations can take place for both the doublet and quartet spin states. Moreover, DMS is more reactive than DMSO, and S-oxidation is more favorable than S-dealkylation, whereas N-dealkylation is more favorable than N-oxidation. This is in perfect agreement with experimental results, showing that density functional activation energies are reliable and comparable for widely different reactions with cytochrome P450.},
  author       = {Rydberg, Patrik and Ryde, Ulf and Olsen, Lars},
  issn         = {1549-9618},
  language     = {eng},
  number       = {8},
  pages        = {1369--1377},
  publisher    = {The American Chemical Society (ACS)},
  series       = {Journal of Chemical Theory and Computation},
  title        = {Sulfoxide, sulfur, and nitrogen oxidation and dealkylation by cytochrome P450},
  url          = {http://dx.doi.org/10.1021/ct800101v},
  doi          = {10.1021/ct800101v},
  volume       = {4},
  year         = {2008},
}