Abstract
During synthrophic growth of Hydrogenophaga palleronii (strain S1) and Agrobacterium radiobacter (strain S2) with 4-aminobenzene sulfonate (4ABS) only strain S1 desaminates 4ABS by regioselective 3,4-dioxygenation. The major part of the metabolite catechol-4-sulfonate (4CS) is excreted and further metabolized by strain S2. Although both organisms harbour activities of protocatechuate pathways assimilation of the structural analog 4CS requires first of all enzyme activities with broader substrate specificity: protocatechuate 3,4-dioxygenase and carboxymuconate cycloisomerase activities were identified which in addition to the natural substrates also convert 4CS and 3-sulfomuconate respectively. 4-Carboxymethyl-4-sulfobut-2-en-4-olide (4SL) was identified as a metabolite. Its further metabolism requires a desulfonating enzyme which eliminates sulfite from (4SL) and generates maleylacetate. Convergence with the 3-oxoadipate pathway is catalyzed by a maleyl acetate reductase, which was identified in cell-free extracts of both organisms S1 and S2. Characteristically, only strain S1 can oxidize sulfite and thus contributes to the interdependence of the two bacteria during growth with 4ABS.
MeSH Terms
Biodegradation, Environmental
Pseudomonas/classification,enzymology,growth & development,metabolism
Rhizobium/classification,enzymology,growth & development,metabolism
Substrate Specificity
Sulfanilic Acids/chemistry,metabolism
Chemicals
Sulfanilic Acids
4-sulfanilic acid
Authors & Affiliations
2 authors, click to expand affiliations / ORCID
Feigel B J
Institut für Mikrobiologie, Universität Stuttgart, Federal Republic of Germany.
Knackmuss H J
References (17)
17 references, click to expand
-
Bacterial communities degrading amino- and hydroxynaphthalene-2-sulfonates.
Appl Environ Microbiol. 1986 Nov;52(5):1195-202
PMID: 3789715
-
Studies on oxygenases; pyrocatechase.
J Biol Chem. 1957 Dec;229(2):905-20
PMID: 13502352
-
Microbial metabolism of aryl sulphonates a re-assessment of colorimetric methods for the determination of sulphite and their use in measuring desulphonation of aryl and alkylbenzene sulphonates.
Antonie Van Leeuwenhoek. 1975;41(4):493-511
PMID: 176938
-
Enzymatic formation, stability, and spontaneous reactions of 4-fluoromuconolactone, a metabolite of the bacterial degradation of 4-fluorobenzoate.
J Bacteriol. 1990 Sep;172(9):5119-29
PMID: 2394680
-
MECHANISM OF BETA-KETOADIPATE FORMATION BY BACTERIA.
Nature. 1964 Dec 26;204:1279-83
PMID: 14254410
-
The enzymatic formation of beta-carboxymuconic acid.
J Biol Chem. 1954 Oct;210(2):809-20
PMID: 13211619
-
Metabolism of phenol and resorcinol in Trichosporon cutaneum.
J Bacteriol. 1979 Jan;137(1):13-21
PMID: 33145
-
Halogenated protocatechuates as substrates for protocatechuate dioxygenase from Pseudomonas cepacia.
J Biol Chem. 1983 Dec 10;258(23):14413-21
PMID: 6643491
-
Protocatechuic acid oxidase.
J Biol Chem. 1954 Oct;210(2):799-808
PMID: 13211618
-
Chemical structure and biodegradability of halogenated aromatic compounds. Conversion of chlorinated muconic acids into maleoylacetic acid.
Biochem J. 1980 Oct 15;192(1):339-47
PMID: 7305906
-
Refinement of the coomassie blue method of protein quantitation. A simple and linear spectrophotometric assay for less than or equal to 0.5 to 50 microgram of protein.
Anal Biochem. 1978 May;86(1):142-6
PMID: 655375
-
The metabolism of aromatic acids by Pseudomonas testosteroni and P. acidovorans.
Arch Mikrobiol. 1967;59(1):302-14
PMID: 5602468
-
A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding.
Anal Biochem. 1976 May 7;72:248-54
PMID: 942051
-
The conversion of catechol and protocatechuate to beta-ketoadipate by Pseudomonas putida. 3. Enzymes of the catechol pathway.
J Biol Chem. 1966 Aug 25;241(16):3795-9
PMID: 5330966
-
Chemical structure and biodegradability of halogenated aromatic compounds. Substituent effects on 1,2-dioxygenation of catechol.
Biochem J. 1978 Jul 15;174(1):85-94
PMID: 697766
-
The conversion of catechol and protocatechuate to beta-ketoadipate by Pseudomonas putida. II. Enzymes of the protocatechuate pathway.
J Biol Chem. 1966 Aug 25;241(16):3787-94
PMID: 5916392
-
The conversion of catechol and protocatechuate to beta-ketoadipate by Pseudomonas putida.
J Biol Chem. 1966 Aug 25;241(16):3776-86
PMID: 5916391