-transparent.png){kind=logo}
The absolute configurations of the enantiomeric 5,6-arene oxides of 7,12-dimethylbenz[a]anthracene (DMBA) were recently assigned such that the late eluting enantiomer from a chiral HPLC column has 5R,6S absolute configuration. [Mushtaq et al. (1984) BBRC 125, 539]. The authors further concluded that the 5R,6S-enantiomer predominates on metabolism of DMBA by cytochrome P450c in liver microsomes from 3-methylcholanthrene-treated rats. Their chemical assignment of absolute configuration is incorrect. Thus, metabolism of DMBA by these microsomes as well as by homogeneous cytochrome P450c produces 5,6-oxide highly enriched (95%) in the 5S,6R-enantiomer in accord with theoretical predictions.
S K Balani, and
H J Yeh, and
D E Ryan, and
P E Thomas, and
W Levin, and
D M Jerina
December 1984,
Biochemical and biophysical research communications,
S K Balani, and
H J Yeh, and
D E Ryan, and
P E Thomas, and
W Levin, and
D M Jerina
July 1975,
Comptes rendus hebdomadaires des seances de l'Academie des sciences. Serie D: Sciences naturelles,
S K Balani, and
H J Yeh, and
D E Ryan, and
P E Thomas, and
W Levin, and
D M Jerina
May 1991,
Cancer letters,
S K Balani, and
H J Yeh, and
D E Ryan, and
P E Thomas, and
W Levin, and
D M Jerina
January 1990,
Chirality,
S K Balani, and
H J Yeh, and
D E Ryan, and
P E Thomas, and
W Levin, and
D M Jerina
March 1989,
Carcinogenesis,
S K Balani, and
H J Yeh, and
D E Ryan, and
P E Thomas, and
W Levin, and
D M Jerina
October 1976,
The Journal of organic chemistry,
S K Balani, and
H J Yeh, and
D E Ryan, and
P E Thomas, and
W Levin, and
D M Jerina
July 1975,
Biochemistry,
S K Balani, and
H J Yeh, and
D E Ryan, and
P E Thomas, and
W Levin, and
D M Jerina
June 1980,
Biochimica et biophysica acta,
S K Balani, and
H J Yeh, and
D E Ryan, and
P E Thomas, and
W Levin, and
D M Jerina
January 1978,
The Journal of organic chemistry,
S K Balani, and
H J Yeh, and
D E Ryan, and
P E Thomas, and
W Levin, and
D M Jerina
September 1974,
Journal of the American Chemical Society,
