DOI: 10.1111/j.1432-1033.1971.tb01406.x. The <i>meta</i> Cleavage of Catechol by <i>Azotobacter</i> Species

The meta Cleavage of Catechol by Azotobacter Species

10.1111/j.1432-1033.1971.tb01406.x

Crossref journal-article

Wiley

European Journal of Biochemistry (311)

Abstract

Catechol was metabolized through 2‐hydroxymuconic semialdehyde by cell‐free extracts of benzoate‐grown Azotobacter Strains. Some properties of catechol 2,3 oxygenase preparations from Azotobacter vinelandii 206 are described. Two different enzymatic activities able to attack 2‐hydroxymuconic semialdehyde have been found in crude extracts from benzoate‐grown cells; one catalyses a hydrolytic release of formate from the semialdehyde and the other a dehydrogenation of this compound to 4‐oxalocrotonate. However, the low, non‐inducible levels of 2‐hydroxymuconic semialdehyde hydrolase activity appear negligible for metabolic purposes and the semialdehyde seems to be dissimilated almost exclusively via 4‐oxalocrotonate, by the action of a NAD+‐dependent dehydrogenase, in Azotobacter strains. A tautomerase activity responsible for the interconversion of the enol and keto forms of 4‐oxalocrotonic acid was found in extracts from benzoate‐grown cells. 4‐Oxalocrotonate was stoicheiometrically converted to CO2 and 4‐hydroxy‐2‐oxovalerate by a partially purified extract, with the transient formation of a compound that appears to be 2‐oxopent‐4‐enoic acid. The 4‐oxalocrotonate decarboxylase activity was stimulated by Mg2+ or Mn2+ ions and was inhibited by EDTA. Cell‐free extracts from Azotobacter strains converted synthetic 4‐hydroxy‐2‐oxovalerate to acetaldehyde and pyruvate. A reaction sequence, termed the 4‐oxalocrotonate pathway, for the dissimiation of catechol to acetaldehyde and pyruvate by Azotobacter species is presented. All the enzymes operative in this pathway were inducible, except the 4‐hydroxy‐2‐oxovalerate aldolase. The findings described here are discussed in connection with the two previously reported meta cleavage pathways for the oxidation of catechol in Pseudomonas strains.

Bibliography

Salaâtrepat, J. M., & Evans, W. C. (1971). The meta Cleavage of Catechol by Azotobacter Species. European Journal of Biochemistry, 20(3), 400â413. Portico.

Authors 2

Jose M. Sala‐trepat (first)
W. Charles Evans (additional)

References 36 Referenced 250

10.1038/188560a0
{'key': 'e_1_2_2_3_2', 'first-page': '287', 'volume-title': 'The Microbiol Metabolism of Phenolics, in Soil Biochemistry', 'author': 'Dagley S.', 'year': '1967'} / The Microbiol Metabolism of Phenolics, in Soil Biochemistry by Dagley S. (1967)
10.1016/S0021-9258(18)99839-X
10.1016/S0021-9258(18)81402-8 / J. Biol. Chem. by Nishizuka Y. (1962)
10.1042/bj0950466
10.1042/bj1110303
10.1042/bj1060859
10.1007/BF00446898
10.1128/jb.100.2.869-877.1969 / J. Bacteriol. by Feist C. F. (1969)
Zubair U. Ph.D. Thesis University of Leeds(1963).
10.1042/bj1010293
10.1099/00221287-59-1-1
10.1039/CT9017901265 / J. Chem. Soc. (London) by Lapworth A. (1901)
10.1002/hlca.19480310226
10.1021/ja01256a039
{'key': 'e_1_2_2_17_2', 'first-page': '40', 'volume-title': 'Organic Synthesis', 'author': 'Marvel C. S.', 'year': '1926'} / Organic Synthesis by Marvel C. S. (1926)
{'key': 'e_1_2_2_18_2', 'first-page': '2184', 'volume': '44', 'author': 'Willstätter R.', 'year': '1911', 'journal-title': 'Ber. Deut. Chem. Ges.'} / Ber. Deut. Chem. Ges. by Willstätter R. (1911)
{'key': 'e_1_2_2_19_2', 'first-page': '4745', 'volume': '37', 'author': 'Willstätter R.', 'year': '1904', 'journal-title': 'Ber. Deut. Chem. Ges.'} / Ber. Deut. Chem. Ges. by Willstätter R. (1904)
{'key': 'e_1_2_2_20_2', 'first-page': '488', 'volume': '42', 'author': 'Dakin H. D.', 'year': '1909', 'journal-title': 'Amer. Chem. J.'} / Amer. Chem. J. by Dakin H. D. (1909)
{'key': 'e_1_2_2_21_2', 'first-page': '4022', 'volume': '37', 'author': 'Biltz H.', 'year': '1904', 'journal-title': 'Chem. Ber.'} / Chem. Ber. by Biltz H. (1904)
10.1099/00221287-44-2-241
10.1099/00221287-56-3-i / J. Gen. Microbiol. by Mather I. (1969)
10.1016/S0076-6879(55)02277-5
{'key': 'e_1_2_2_25_2', 'volume-title': 'Manometric Techniques', 'author': 'Umbreit W. W.', 'year': '1957'} / Manometric Techniques by Umbreit W. W. (1957)
10.1021/ac60015a025
10.1042/bj0550416
10.1016/0076-6879(55)01102-6 / Methods in Enzymology by Rose I. R. (1955)
10.1016/S0021-9258(18)57021-6
10.1016/S0021-9258(19)52451-6
10.1016/S0021-9258(18)64061-X
{'key': 'e_1_2_2_32_2', 'first-page': '582', 'volume': '338', 'author': 'Nozaki M.', 'year': '1963', 'journal-title': 'Biochem. Z.'} / Biochem. Z. by Nozaki M. (1963)
10.1016/0005-2744(70)90007-0
10.1099/00221287-44-2-221
10.1016/S0021-9258(18)64866-5
Sala‐Trepat J. M. unpublished observations.
Catterall A. Sala‐Trepat J. M. andWilliams P. A. Biochem. Biophys. Res. Commun. in press.

Dates

Type	When
Created	20 years, 6 months ago (March 3, 2005, 9:14 a.m.)
Deposited	1 year, 9 months ago (Nov. 23, 2023, 7 a.m.)
Indexed	3 weeks, 3 days ago (Aug. 12, 2025, 5:37 p.m.)
Issued	54 years, 3 months ago (June 1, 1971)
Published	54 years, 3 months ago (June 1, 1971)
Published Online	20 years, 6 months ago (March 3, 2005)
Published Print	54 years, 3 months ago (June 1, 1971)

Funders 0

None

BibTeX

@article{Sala_trepat_1971, title={The meta Cleavage of Catechol by Azotobacter Species: 4‐Oxalocrotonate Pathway}, volume={20}, ISSN={1432-1033}, url={http://dx.doi.org/10.1111/j.1432-1033.1971.tb01406.x}, DOI={10.1111/j.1432-1033.1971.tb01406.x}, number={3}, journal={European Journal of Biochemistry}, publisher={Wiley}, author={Sala‐trepat, Jose M. and Evans, W. Charles}, year={1971}, month=jun, pages={400–413} }

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