AI Article Synopsis
- The study investigated how butylbenzene is oxidized by rat liver enzymes, focusing on where the oxidation occurs on the molecule (regioselectivity) and the specific configurations of the resulting products (stereoselectivity).
- When incubated with rat liver enzymes, the oxidation led to the formation of specific alcohols, with a higher yield of certain isomers (like (R)- and (S)-alcohols) and butanediols, showcasing a preference for particular chemical structures.
- The process was influenced by substances like phenobarbital and beta-napthoflavone, and notable differences were observed between male and female rats, indicating potential variations in metabolic responses.
Article Abstract
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.
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