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:
https://lup.lub.lu.se/record/1252833
- author
- Rydberg, Patrik
; Ryde, Ulf
LU
and Olsen, Lars
- organization
- publishing date
- 2008
- 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
- 2023-02-09 02:36:16
@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 = {{https://lup.lub.lu.se/search/files/137150924/110_nsox.pdf}},
doi = {{10.1021/ct800101v}},
volume = {{4}},
year = {{2008}},
}