Literature DB >> 16535266

Biotransformation of 6,6-Dimethylfulvene by Pseudomonas putida RE213.

R W Eaton, S A Selifonov.   

Abstract

The biotransformation of 6,6-dimethylfulvene [5-(1-methylethylidene)-1,3-cyclopentadiene], a nonaromatic C(inf5) carbocyclic analog of isopropylbenzene, was examined by using Pseudomonas putida RE213, a Tn5-generated dihydrodiol-accumulating mutant of the isopropylbenzene-degrading strain P. putida RE204. 6,6-Dimethylfulvene was converted to a single chiral product identified as (+)-(1R,2S)-cis-1,2-dihydroxy-5-(1-methylethylidene)-3-cyclopentene. This isopropylbenzene 2,3-dioxygenase-catalyzed transformation demonstrates the potential of bacterial arene dioxygenases for the direct conversion of cyclopentadienylidene compounds to homochiral C(inf5) carbocyclic cis-diols for use in enantiocontrolled organic syntheses.

Entities:  

Year:  1996        PMID： 16535266      PMCID： PMC1388791          DOI： 10.1128/aem.62.3.756-760.1996

Source DB:  PubMed          Journal:  Appl Environ Microbiol        ISSN： 0099-2240            Impact factor:   4.792


  17 in total

1.  The p-cymene pathway in Pseudomonas putida PL: isolation of a dihydrodiol accumulated by a mutant.

Authors:  J J Defrank; D W Ribbons
Journal:  Biochem Biophys Res Commun       Date:  1976-06-21       Impact factor: 3.575

2.  Metabolism of benzoic acid by bacteria. Accumulation of (-)-3,5-cyclohexadiene-1,2-diol-1-carboxylic acid by mutant strain of Alcaligenes eutrophus.

Authors:  A M Reiner; G D Hegeman
Journal:  Biochemistry       Date:  1971-06-22       Impact factor: 3.162

3.  Absolute stereochemistry of the (+)-cis-1,2-dihydroxy-3-methylcyclohexa-3,5-diene produced from toluene by Pseudomonas putida.

Authors:  H Ziffer; D M Jerina; D T Gibson; V M Kobal
Journal:  J Am Chem Soc       Date:  1973-06-13       Impact factor: 15.419

4.  Initial reactions in the oxidation of ethylbenzene by Pseudomonas putida.

Authors:  D T Gibson; B Gschwendt; W K Yeh; V M Kobal
Journal:  Biochemistry       Date:  1973-04-10       Impact factor: 3.162

5.  X-ray determination of the absolute stereochemistry of the initial oxidation product formed from toluene by Pseudomonas puida 39-D.

Authors:  V M Kobal; D T Gibson; R E Davis; A Garza
Journal:  J Am Chem Soc       Date:  1973-06-27       Impact factor: 15.419

6.  Biotransformation of benzothiophene by isopropylbenzene-degrading bacteria.

Authors:  R W Eaton; J D Nitterauer
Journal:  J Bacteriol       Date:  1994-07       Impact factor: 3.490

7.  Dioxygenolytic cleavage of aryl ether bonds: 1,2-dihydro-1,2-dihydroxy-4-carboxybenzophenone as evidence for initial 1,2-dioxygenation in 3- and 4-carboxy biphenyl ether degradation.

Authors:  K H Engesser; W Fietz; P Fischer; P Schulte; H J Knackmuss
Journal:  FEMS Microbiol Lett       Date:  1990-06-01       Impact factor: 2.742

8.  Regioselective dioxygenation of ortho-trifluoromethylbenzoate by Pseudomonas aeruginosa 142: evidence for 1,2-dioxygenation as a mechanism in ortho-halobenzoate dehalogenation.

Authors:  S A Selifonov; J E Gurst; L P Wackett
Journal:  Biochem Biophys Res Commun       Date:  1995-08-24       Impact factor: 3.575

9.  p-cymene pathway in Pseudomonas putida: initial reactions.

Authors:  J J DeFrank; D W Ribbons
Journal:  J Bacteriol       Date:  1977-03       Impact factor: 3.490

10.  Isolation and characterization of (+)-1,1a-dihydroxy-1-hydrofluoren-9-one formed by angular dioxygenation in the bacterial catabolism of fluorene.

Authors:  S A Selifonov; M Grifoll; J E Gurst; P J Chapman
Journal:  Biochem Biophys Res Commun       Date:  1993-05-28       Impact factor: 3.575
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  1 in total

1.  Regio- and stereospecific oxidation of fluorene, dibenzofuran, and dibenzothiophene by naphthalene dioxygenase from Pseudomonas sp. strain NCIB 9816-4.

Authors:  S M Resnick; D T Gibson
Journal:  Appl Environ Microbiol       Date:  1996-11       Impact factor: 4.792
  1 in total

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