Literature DB >> 6083780

Stereochemistry of 1-(4'-hydroxyphenyl)ethanol produced by hydroxylation of 4-ethylphenol by p-cresol methylhydroxylase.

W McIntire, D J Hopper, J C Craig, E T Everhart, R V Webster, M J Causer, T P Singer.   

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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Year:  1984        PMID： 6083780      PMCID： PMC1144472          DOI： 10.1042/bj2240617

Source DB:  PubMed          Journal:  Biochem J        ISSN： 0264-6021            Impact factor:   3.857


  9 in total

1.  An instance of partially asymmetric enzymatic synthesis.

Authors:  T P SINGER
Journal:  Biochim Biophys Acta       Date:  1952-01

2.  Investigation of the mechanism of the methylmalonyl-CoA mutase reaction with the substrate analogue: ethylmalonyl-CoA.

Authors:  J Rétey; E H Smith; B Zagalak
Journal:  Eur J Biochem       Date:  1978-02

3.  The purification and properties of p-cresol-(acceptor) oxidoreductase (hydroxylating), a flavocytochrome from Pseudomonas putida.

Authors:  D J Hopper; D G Taylor
Journal:  Biochem J       Date:  1977-10-01       Impact factor: 3.857

4.  Enantiomeric specificity of glyceraldehyde 3-phosphate dehydrogenase.

Authors:  L D Byers
Journal:  Arch Biochem Biophys       Date:  1978-03       Impact factor: 4.013

5.  Stereochemical outcome of processing of fluorinated substrates by ATP citrate lyase and malate synthase.

Authors:  M A Marletta; P A Srere; C Walsh
Journal:  Biochemistry       Date:  1981-06-23       Impact factor: 3.162

6.  Incorporation of [18O]water in the formation of p-hydroxybenzyl alcohol by the p-cresol methylhydroxylase from Pseudomonas putida.

Authors:  D J Hopper
Journal:  Biochem J       Date:  1978-10-01       Impact factor: 3.857

7.  8 alpha-(O-Tyrosyl)flavin adenine dinucleotide, the prosthetic group of bacterial p-cresol methylhydroxylase.

Authors:  W McIntire; D E Edmondson; D J Hopper; T P Singer
Journal:  Biochemistry       Date:  1981-05-26       Impact factor: 3.162

8.  P-cresol and 3,5-xylenol methylhydroxylases in Pseudomonas putida N.C.I.B. 9896.

Authors:  M J Keat; D J Hopper
Journal:  Biochem J       Date:  1978-11-01       Impact factor: 3.857

9.  The specificities and configurations of ternary complexes of yeast and liver alcohol dehydrogenases.

Authors:  F M Dickinson; K Dalziel
Journal:  Biochem J       Date:  1967-07       Impact factor: 3.857
  9 in total
  10 in total

1.  p-Cresol methylhydroxylase. Assay and general properties.

Authors:  W McIntire; D J Hopper; T P Singer
Journal:  Biochem J       Date:  1985-06-01       Impact factor: 3.857

2.  Formation and properties of flavoprotein-cytochrome hybrids by recombination of subunits from different species.

Authors:  S C Koerber; D J Hopper; W S McIntire; T P Singer
Journal:  Biochem J       Date:  1985-10-15       Impact factor: 3.857

3.  Isolation and characterization of a novel Rhodococcus strain with switchable carbonyl reductase and para-acetylphenol hydroxylase activities.

Authors:  Rui Zhang; Jie Ren; Yu Wang; Qiaqing Wu; Min Wang; Dunming Zhu
Journal:  J Ind Microbiol Biotechnol       Date:  2012-09-27       Impact factor: 3.346

4.  Stereochemical aspects of the oxidation of 4-ethylphenol by the bacterial enzyme 4-ethylphenol methylenehydroxylase.

Authors:  C D Reeve; M A Carver; D J Hopper
Journal:  Biochem J       Date:  1990-08-01       Impact factor: 3.857

5.  Inversion of stereospecificity of vanillyl-alcohol oxidase.

Authors:  R H van Den Heuvel; M W Fraaije; M Ferrer; A Mattevi; W J van Berkel
Journal:  Proc Natl Acad Sci U S A       Date:  2000-08-15       Impact factor: 11.205

6.  The purification and characterization of 4-ethylphenol methylenehydroxylase, a flavocytochrome from Pseudomonas putida JD1.

Authors:  C D Reeve; M A Carver; D J Hopper
Journal:  Biochem J       Date:  1989-10-15       Impact factor: 3.857

7.  Regio- and stereospecific conversion of 4-alkylphenols by the covalent flavoprotein vanillyl-alcohol oxidase.

Authors:  R H van den Heuvel; M W Fraaije; C Laane; W J van Berkel
Journal:  J Bacteriol       Date:  1998-11       Impact factor: 3.490

8.  Alkylphenol biotransformations catalyzed by 4-ethylphenol methylenehydroxylase.

Authors:  David J Hopper; Lisa Cottrell
Journal:  Appl Environ Microbiol       Date:  2003-06       Impact factor: 4.792

9.  Purification and characterization of a ferulic acid decarboxylase from Pseudomonas fluorescens.

Authors:  Z Huang; L Dostal; J P Rosazza
Journal:  J Bacteriol       Date:  1994-10       Impact factor: 3.490

10.  Cloning, sequencing, and expression of the structural genes for the cytochrome and flavoprotein subunits of p-cresol methylhydroxylase from two strains of Pseudomonas putida.

Authors:  J Kim; J H Fuller; G Cecchini; W S McIntire
Journal:  J Bacteriol       Date:  1994-10       Impact factor: 3.490
  10 in total

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