Regio- and stereo-selective oxidation of phenylbutane by rat liver.
Regio- and stereo-selective oxidation of butylbenzene (1) has been examined in vitro by rat liver supernatant fraction(S-9). When phenylbutane (1 ) was incubated at 37 degrees C for 1 hr with S-9, asymmetric oxidation occurred regioselectively at benzylic and omega-1 positions to afford preferentially (R)- and (S)-alcohol (2, 4), respectively. This enzymatic propensity was the case for the production of 1, 3-diols. (1R, 3S)- or (1R, 3R)-Butanediols(3a, 3b) were also obtained at 87% and 27%, respectively. This oxidation was induced by phenobarbital (PB) or beta-napthoflavone(beta-NF), and significant sex-related differences in control and PB pre-treated rats have been observed. Since these oxidations were inhibited with SKF-525A and CO, it was inferred that cytochrome P-450 was responsible for the oxidation.
Takeshita
M
M
Tohoku College of Pharmacy, Sendai, Japan.
Miura
M
M
Unuma
Y
Y
Iwai
S
S
Sato
I
I
Arai
T
T
Kosaka
K
K
D000818:Animals; D001555:Benzene Derivatives / Q000378:metabolism*; D002073:Butanes / Q000378:metabolism*; D004789:Enzyme Activation; D005260:Female; D008099:Liver / Q000378:metabolism*; D008297:Male; D010084:Oxidation-Reduction; D051381:Rats; D017208:Rats, Wistar; D012737:Sex Factors; D013237:Stereoisomerism; D015262:Xenobiotics / Q000378:metabolism*
D001555:Benzene Derivatives; D002073:Butanes; D015262:Xenobiotics; C053761:n-butylbenzene