The metabolism of p-fluorophenylacetic acid by a Pseudomonas sp. II. The degradative pathway

1971 ◽  
Vol 17 (5) ◽  
pp. 645-650 ◽  
Author(s):  
D. B. Harper ◽  
E. R. Blakley
Keyword(s):  
Aromatic Ring ◽  
Hydrogen Fluoride ◽  
Phenylacetic Acid ◽  
Oxidative Cleavage ◽  
Cell Suspensions ◽  
Ring Cleavage ◽  
Pseudomonas Sp ◽  
Partial Reduction ◽  
Degradative Pathway ◽  
Unstable Compound

A Pseudomonas sp. grown on p-fluorophenylacetic acid is adapted to the metabolism of phenylacetic acid, 3-fluoro-3-hexenedioic acid, monofluorosuccinic acid, monofluorofumaric acid, β-ketoadipic acid, and β-hydroxyadipic acid. Cell suspensions catalyze the lactonization of 3-fluoro-3-hexenedioic acid to give 4-carboxymethyl-4-fluorobutanolide. The results suggest that 3-fluoro-3-hexenedioic acid is an intermediate in the degradation of p-fluorophenylacetic acid, and may be metabolized by two alternate pathways, depending on the lactone formed. 4-Carboxymethyl-4-fluorobutanolide may be hydrolyzed to give 3-hydroxy-3-fluoroadipic acid, which spontaneously eliminates hydrogen fluoride to give β-ketoadipic acid. Alternatively, 3-fluoro-3-hexenedioic acid may lactonize to form 4-carboxymethyl-3-fluorobutanolide, which is then hydrolyzed to 3-keto-4-fluoroadipic and cleaved to form acetate and monofluorosuccinic acid. The latter is converted to fluorofumaric acid by fumarase to give 2-fluoromalic acid. This unstable compound decomposes to oxaloacetate and hydrogen fluoride. The mechanism of ring cleavage and the mode of formation of 3-fluoro-3-hexenedioic acid are uncertain but may involve partial reduction of the aromatic ring before oxidative cleavage.

scholarly journals The degradative pathway of the s-triazine melamine. The steps to ring cleavage

1982 ◽  
Vol 208 (3) ◽  
pp. 679-684 ◽  
Author(s):  
K Jutzi ◽  
A M Cook ◽  
R Hütter
Keyword(s):  
Enzyme Preparation ◽  
Cyanuric Acid ◽  
Deae Cellulose ◽  
Sole Source ◽  
Ring Cleavage ◽  
Pseudomonas Sp ◽  
Degradative Pathway ◽  
Degradative Enzymes ◽  
Specific Activities ◽  
Transient Intermediate

1. The degradative pathway of melamine (1,3,5-triazine-2,4,6-triamine) was examined in Pseudomonas sp. strain A. 2. The bacterium grew with melamine, ammeline, ammelide, cyanuric acid or NH+4 as sole source of nitrogen, and each substrate was entirely metabolized. Utilization of ammeline, ammelide, cyanuric acid or NH+4 was concomitant with growth. But with melamine as substrate, a transient intermediate was detected, which was identified as ammeline by three methods. 3. Enzymes from strain A were separated by chromatography on DEAE-cellulose, and four activities were examined. 4. Melamine was converted stoichiometrically into equimolar amounts of ammeline and NH+4. 5. Ammeline was converted stoichiometrically into equimolar amounts of ammelide and NH+4; ammelide was identified by four methods. 6. Ammelide was converted stoichiometrically into equimolar amounts of cyanuric acid and NH+4; cyanuric acid was identified by four methods. 7. Cyanuric acid was converted by an enzyme preparation into an unidentified product with negligible release of NH+4. 8. The specific activities of the degradative enzymes (greater than or equal to 0.3 mkat/kg of protein) were high enough to explain the growth rate of the organism. 9. The bacterium converted 0.4 mM-melamine anaerobically into 2.3 mM-NH+4. 10. Two other pseudomonads and two strains of Klebsiella pneumoniae were also examined, with similar results. 11. The degradative pathway of melamine appears to be hydrolytic, and proceeds by three successive deaminations to cyanuric acid, which is further metabolized.

scholarly journals Ring cleavage and degradative pathway of cyanuric acid in bacteria

1985 ◽  
Vol 231 (1) ◽  
pp. 25-30 ◽  
Author(s):  
A M Cook ◽  
P Beilstein ◽  
H Grossenbacher ◽  
R Hütter
Keyword(s):  
Klebsiella Pneumoniae ◽  
Cyanuric Acid ◽  
Deae Cellulose ◽  
Sole Source ◽  
Ring Cleavage ◽  
Pseudomonas Sp ◽  
Degradative Pathway ◽  
Anoxic Conditions

The degradative pathway of cyanuric acid [1,3,5-triazine-2,4,6(1H,3H,5H)-trione] was examined in Pseudomonas sp. strain D. The bacterium grew with cyanuric acid, biuret, urea or NH4+ as sole source of nitrogen, and each substrate was entirely metabolized concomitantly with growth. Enzymes from strain D were separated by chromatography on DEAE-cellulose and three reactions were examined. Cyanuric acid (1 mol) was converted stoichiometrically into 1.0 mol of CO2 and 1.1 mol of biuret, which was conclusively identified. Biuret (1 mol) was converted stoichiometrically into 1.1 mol of NH4+, about 1 mol of CO2 and 1.0 mol of urea, which was conclusively identified. Urea (1 mol) was converted into 1.9 mol of NH4+ and 1.0 mol of CO2. The reactions proceeded under aerobic or anoxic conditions and were presumed to be hydrolytic. Data indicate that the same pathway occurred in another pseudomonad and a strain of Klebsiella pneumoniae.

Mechanism of aromatic ring cleavage of a .beta.-biphenylyl ether dimer catalyzed by lignin peroxidase of Phanerochaete chrysosporium

Biochemistry ◽  
1988 ◽  
Vol 27 (13) ◽  
pp. 4787-4794 ◽  
Author(s):  
Keiji Miki ◽  
Ryuichiro Kondo ◽  
V. Renganathan ◽  
Mary B. Mayfield ◽  
Michael H. Gold
Keyword(s):  
Aromatic Ring ◽  
Phanerochaete Chrysosporium ◽  
Lignin Peroxidase ◽  
Ring Cleavage ◽  
Aromatic Ring Cleavage

Biochemical pathway and degradation of phthalate ester isomers by bacteria

2005 ◽  
Vol 52 (8) ◽  
pp. 241-248 ◽  
Author(s):  
J.-D. Gu ◽  
J. Li ◽  
Y. Wang
Keyword(s):  
Aromatic Ring ◽  
Enrichment Culture ◽  
Klebsiella Oxytoca ◽  
Sole Source ◽  
Phthalate Ester ◽  
Ring Cleavage ◽  
Mangrove Sediment ◽  
Individual Species ◽  
Dimethyl Phthalate ◽  
Dimethyl Phthalate Ester

Degradation of dimethyl isophthalate (DMI) and dimethyl phthalate ester (DMPE) was investigated using microorganisms isolated from mangrove sediment of Hong Kong Mai Po Nature Reserve. One enrichment culture was capable of utilizing DMI as the sole source of carbon and energy, but none of the bacteria in the enrichment culture was capable of degrading DMI alone. In co-culture of two bacteria, degradation was observed proceeding through monomethyl isophthalate (MMI) ester and isophthalic acid (IPA) before the aromatic ring opening. Using DMI as the sole carbon and energy source, Klebsiella oxytoca Sc and Methylobacterium mesophilicum Sr degraded DMI through the biochemical cooperation. The initial hydrolytic reaction of the ester bond was by K. oxytoca Sc and the next step of transformation was by M. mesophilicum Sr, and IPA was degraded by both of them. In another investigation, a novel bacterium, strain MPsc, was isolated for degradation of dimethyl phthalate ester (DMPE) also from the mangrove sediment. On the basis of phenotypic, biochemical and 16S rDNA gene sequence analyses, the strain MPsc should be considered as a new bacterium at the genus level (8% differences). This strain, together with a Rhodococcus zopfii isolated from the same mangrove sediment, was able to degrade DMPE aerobically. The consortium consisting of the two species degraded 450mg/l DMPE within 3 days as the sole source of carbon and energy, but none of the individual species alone was able to transform DMPE. Furthermore, the biochemical degradation pathway proceeded through monomethyl phthalate (MMP), phthalic acid (PA) and then protocatechuate before aromatic ring cleavage. Our results suggest that degradation of complex organic compounds including DMI and DMPE may be carried out by several members of microorganisms working together in the natural environments.

scholarly journals Enzymology of oxidation of tropic acid to phenylacetic acid in metabolism of atropine by Pseudomonas sp. strain AT3.

1997 ◽  
Vol 179 (4) ◽  
pp. 1044-1050 ◽  
Author(s):  
M T Long ◽  
B A Bartholomew ◽  
M J Smith ◽  
P W Trudgill ◽  
D J Hopper
Keyword(s):  
Phenylacetic Acid ◽  
Pseudomonas Sp ◽  
Tropic Acid

scholarly journals Aromatic ring cleavage of a β-biphenyl ether dimer catalyzed by lignin peroxidase of phanerochaete chrysosporium

FEBS Letters ◽  
1987 ◽  
Vol 210 (2) ◽  
pp. 199-203 ◽  
Author(s):  
Keiji Miki ◽  
V. Renganathan ◽  
Mary B. Mayfield ◽  
Michael H. Gold
Keyword(s):  
Aromatic Ring ◽  
Phanerochaete Chrysosporium ◽  
Lignin Peroxidase ◽  
Ring Cleavage ◽  
Aromatic Ring Cleavage
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