Stereoselective formation of benzo(c)phenanthrene (+)-(3S,4R) and (+)-(5S,6R)-oxides by cytochrome P450c in a highly purified and reconstituted system
P J van Bladeren
1
,
S K Balani
1
,
J M Sayer
1
,
Dhiren R. Thakker
1
,
D. R. Boyd
2
,
D E Ryah
3
,
P.E. Thomas
3
,
W. LEVIN
3
,
D M Jerina
1
2
Department of Chemistry, The Queen's University of Belfast, Belfast, BT9 5AG, N. Ireland.
|
3
Laboratory of Experimental Carcinogenesis and Metabolism, Roche Institute of Molecular Biology, Nutley, NJ 07110 USA
|
Publication type: Journal Article
Publication date: 1987-05-01
scimago Q2
wos Q3
SJR: 0.748
CiteScore: 4.9
Impact factor: 2.2
ISSN: 0006291X, 10902104
PubMed ID:
3109408
Biochemistry
Molecular Biology
Cell Biology
Biophysics
Abstract
The principal oxidative metabolites formed from benzo(c)phenanthrene (B(c)Ph) by the cytochromes P450 in liver microsomes from control and treated rats are the 3,4- and 5,6-arene oxides. A procedure is described which allows determination of the enantiomer composition and absolute configuration of these arene oxides based on HPLC separation of isomeric thiolate adducts formed with N-acetyl-L-cysteine in base. Incubation of [ 3 H]-B(c)Ph with highly purified cytochrome P450c in a reconstituted monooxygenase system followed by trapping of the metabolically formed arene oxides as above indicated that the 3,4-oxide was predominantly the (+)-(3S,4R)-enantiomer (90%) and that the 5,6-oxide consisted mainly of the (+)-(5S,6R)-enantiomer (76%). The results are discussed in terms of their implications about the catalytic binding site of cytochrome P450c.
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van Bladeren P. J. et al. Stereoselective formation of benzo(c)phenanthrene (+)-(3S,4R) and (+)-(5S,6R)-oxides by cytochrome P450c in a highly purified and reconstituted system // Biochemical and Biophysical Research Communications. 1987. Vol. 145. No. 1. pp. 160-167.
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van Bladeren P. J., Balani S. K., Sayer J. M., Thakker D. R., Boyd D. R., Ryah D. E., Thomas P., LEVIN W., Jerina D. M. Stereoselective formation of benzo(c)phenanthrene (+)-(3S,4R) and (+)-(5S,6R)-oxides by cytochrome P450c in a highly purified and reconstituted system // Biochemical and Biophysical Research Communications. 1987. Vol. 145. No. 1. pp. 160-167.
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TY - JOUR
DO - 10.1016/0006-291x(87)91301-5
UR - https://doi.org/10.1016/0006-291x(87)91301-5
TI - Stereoselective formation of benzo(c)phenanthrene (+)-(3S,4R) and (+)-(5S,6R)-oxides by cytochrome P450c in a highly purified and reconstituted system
T2 - Biochemical and Biophysical Research Communications
AU - van Bladeren, P J
AU - Balani, S K
AU - Sayer, J M
AU - Thakker, Dhiren R.
AU - Boyd, D. R.
AU - Ryah, D E
AU - Thomas, P.E.
AU - LEVIN, W.
AU - Jerina, D M
PY - 1987
DA - 1987/05/01
PB - Elsevier
SP - 160-167
IS - 1
VL - 145
PMID - 3109408
SN - 0006-291X
SN - 1090-2104
ER -
Cite this
BibTex (up to 50 authors)
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@article{1987_van Bladeren,
author = {P J van Bladeren and S K Balani and J M Sayer and Dhiren R. Thakker and D. R. Boyd and D E Ryah and P.E. Thomas and W. LEVIN and D M Jerina},
title = {Stereoselective formation of benzo(c)phenanthrene (+)-(3S,4R) and (+)-(5S,6R)-oxides by cytochrome P450c in a highly purified and reconstituted system},
journal = {Biochemical and Biophysical Research Communications},
year = {1987},
volume = {145},
publisher = {Elsevier},
month = {may},
url = {https://doi.org/10.1016/0006-291x(87)91301-5},
number = {1},
pages = {160--167},
doi = {10.1016/0006-291x(87)91301-5}
}
Cite this
MLA
Copy
van Bladeren, P. J., et al. “Stereoselective formation of benzo(c)phenanthrene (+)-(3S,4R) and (+)-(5S,6R)-oxides by cytochrome P450c in a highly purified and reconstituted system.” Biochemical and Biophysical Research Communications, vol. 145, no. 1, May. 1987, pp. 160-167. https://doi.org/10.1016/0006-291x(87)91301-5.