Abstract
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.
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- Byers L. D. Enantiomeric specificity of glyceraldehyde 3-phosphate dehydrogenase. Arch Biochem Biophys. 1978 Mar;186(2):335–342. doi: 10.1016/0003-9861(78)90443-5. [DOI] [PubMed] [Google Scholar]
- Dickinson F. M., Dalziel K. The specificities and configurations of ternary complexes of yeast and liver alcohol dehydrogenases. Biochem J. 1967 Jul;104(1):165–172. doi: 10.1042/bj1040165. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Hopper D. J. Incorporation of [18O]water in the formation of p-hydroxybenzyl alcohol by the p-cresol methylhydroxylase from Pseudomonas putida. Biochem J. 1978 Oct 1;175(1):345–347. doi: 10.1042/bj1750345. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Hopper D. J., Taylor D. G. The purification and properties of p-cresol-(acceptor) oxidoreductase (hydroxylating), a flavocytochrome from Pseudomonas putida. Biochem J. 1977 Oct 1;167(1):155–162. doi: 10.1042/bj1670155. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Keat M. J., Hopper D. J. P-cresol and 3,5-xylenol methylhydroxylases in Pseudomonas putida N.C.I.B. 9896. Biochem J. 1978 Nov 1;175(2):649–658. doi: 10.1042/bj1750649. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Marletta M. A., Srere P. A., Walsh C. Stereochemical outcome of processing of fluorinated substrates by ATP citrate lyase and malate synthase. Biochemistry. 1981 Jun 23;20(13):3719–3723. doi: 10.1021/bi00516a008. [DOI] [PubMed] [Google Scholar]
- McIntire W., Edmondson D. E., Hopper D. J., Singer T. P. 8 alpha-(O-Tyrosyl)flavin adenine dinucleotide, the prosthetic group of bacterial p-cresol methylhydroxylase. Biochemistry. 1981 May 26;20(11):3068–3075. doi: 10.1021/bi00514a013. [DOI] [PubMed] [Google Scholar]
- Rétey J., Smith E. H., Zagalak B. Investigation of the mechanism of the methylmalonyl-CoA mutase reaction with the substrate analogue: ethylmalonyl-CoA. Eur J Biochem. 1978 Feb;83(2):437–451. doi: 10.1111/j.1432-1033.1978.tb12110.x. [DOI] [PubMed] [Google Scholar]
- SINGER T. P. An instance of partially asymmetric enzymatic synthesis. Biochim Biophys Acta. 1952 Jan;8(1):108–109. doi: 10.1016/0006-3002(52)90015-2. [DOI] [PubMed] [Google Scholar]