| dc.contributor |
Wichita State University. Department of Chemistry |
en_US |
| dc.contributor.author |
Bhakta, Mehul N. |
en_US |
| dc.contributor.author |
Hollenberg, Paul F. |
en_US |
| dc.contributor.author |
Wimalasena, Kandatege |
en_US |
| dc.date.accessioned |
2012-02-06T17:17:08Z |
|
| dc.date.available |
2012-02-06T17:17:08Z |
|
| dc.date.issued |
2005-02-09 |
en_US |
| dc.identifier |
15686361 |
en_US |
| dc.identifier |
7503056 |
en_US |
| dc.identifier |
CA 16954/ GM 45026 |
en_US |
| dc.identifier.citation |
Journal of the American Chemical Society. 2005 Feb 9; 127(5): 1376-7. |
en_US |
| dc.identifier.issn |
0002-7863 |
en_US |
| dc.identifier.uri |
http://dx.doi.org/10.1021/ja0436143 |
en_US |
| dc.identifier.uri |
http://hdl.handle.net/10057/4399 |
|
| dc.description |
Click on the DOI link below to access the article (may not be free). |
en_US |
| dc.description.abstract |
A high-valent iron-oxo species analogous to the compound I of peroxidases has been thought to be the activated oxygen species in P450-catalyzed reactions. Spectroscopic characterization of the catalytically competent iron-oxo species in iodosobenzene (PhIO)-supported model reactions and parallels between these model reactions and PhIO- and NADPH/O2-supported P450 reactions have been taken as strong evidence for this proposal. To support this proposal, subtle differences observed in regio- and chemoselectivities, isotope effects, and source of oxygen, etc., between NADPH/O2- and PhIO-supported P450 reactions have been generally attributed to reasons other than the mechanistic differences between the two systems. In the present study, we have used a series of sensitive mechanistic probes, 4-chloro-N-cyclopropyl-N-alkylanilines, to compare and contrast the chemistries of the NADPH/O2- and PhIO-supported purified CYP2B1 N-dealkylation reactions. Herein we present the first experimental evidence to demonstrate that the NADPH/O2- and PhIO-supported P450 N-dealkylations are mechanistically distinct and, thus, the P450/PhIO system may not be a good mechanistic model for P450/NADPH/O2-catalyzed N-dealkylations. |
en_US |
| dc.description.sponsorship |
NCI NIH HHS/ NIGMS NIH HHS |
en_US |
| dc.format.extent |
1376-7 |
en_US |
| dc.language.iso |
eng |
en_US |
| dc.publisher |
American Chemical Society |
en_US |
| dc.relation.ispartofseries |
Journal of the American Chemical Society |
en_US |
| dc.relation.ispartofseries |
J. Am. Chem. Soc. |
en_US |
| dc.source |
NLM |
en_US |
| dc.subject |
Research Support, U.S. Gov't, P.H.S. |
en_US |
| dc.subject.mesh |
Alkylation |
en_US |
| dc.subject.mesh |
Catalysis |
en_US |
| dc.subject.mesh |
Cytochrome P-450 CYP2B1/chemistry |
en_US |
| dc.subject.mesh |
Iodobenzenes/chemistry |
en_US |
| dc.subject.mesh |
NADP/chemistry |
en_US |
| dc.subject.mesh |
Oxidation-Reduction |
en_US |
| dc.subject.mesh |
Oxygen/chemistry |
en_US |
| dc.subject.mesh |
Cytochrome P-450 CYP2B1/metabolism |
en_US |
| dc.subject.mesh |
Iodobenzenes/metabolism |
en_US |
| dc.subject.mesh |
NADP/metabolism |
en_US |
| dc.subject.mesh |
Oxygen/metabolism |
en_US |
| dc.title |
P(450)/NADPH/O(2)- and P(450)/PhIO-catalyzed N-dealkylations are mechanistically distinct |
en_US |
| dc.type |
Article |
en_US |
| dc.coverage.spacial |
United States |
en_US |
| dc.description.version |
peer reviewed |
en_US |
| dc.rights.holder |
Copyright © 2005 American Chemical Society |
en_US |