Stereochemistry of 1-(4'-hydroxyphenyl)ethanol produced by hydroxylation of 4-ethylphenol by p-cresol methylhydroxylase.
Enzymic hydroxylation of 4-ethylphenol by (a) Pseudomonas putida and (b) highly purified p-cresol methylhydroxylase gave optically active 1-(4'-hydroxyphenyl)-ethanol. The products were transformed into the phenolic methyl ethers and shown to contain 69.5% and 65.6%, respectively, of the (S)-(-)-isomer. The stereochemistry of the reaction is discussed in terms of three distinct steps occurring at the active site of the enzyme.
D000431:Ethanol / Q000031:analogs & derivatives*; D006900:Hydroxylation; D006899:Mixed Function Oxygenases / Q000378:metabolism*; D008968:Molecular Conformation; D010636:Phenols / Q000378:metabolism*; D010626:Phenylethyl Alcohol / Q000031:analogs & derivatives* / Q000378:metabolism; D011549:Pseudomonas / Q000378:metabolism; D013237:Stereoisomerism
D010636:Phenols; C011867:4-hydroxyphenylethanol; D000431:Ethanol; C042291:4-ethylphenol; D006899:Mixed Function Oxygenases; C019947:p-cresol oxidoreductase; D010626:Phenylethyl Alcohol