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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.
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author
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
external identifiers
  • wos:000258400600022
  • scopus:58149157800
ISSN
1549-9618
DOI
10.1021/ct800101v
language
English
LU publication?
yes
id
4ab432cc-1ccc-46ae-8756-c907340915ea (old id 1252833)
date added to LUP
2008-11-03 15:41:39
date last changed
2017-09-10 03:31:57
@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},
  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},
  volume       = {4},
  year         = {2008},
}