| Metabolism of 4-amino-3-hydroxybenzoic acid by Bordetella sp. strain 10d: A different modified meta-cleavage pathway for 2-aminophenols. | |
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MedLine Citation:
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PMID: 17090920 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Bordetella sp. strain 10d metabolizes 4-amino-3-hydroxybenzoic acid via 2-hydroxymuconic 6-semialdehyde. Cell extracts from 4-amino-3-hydroxybenzoate-grown cells showed high NAD(+)-dependent 2-hydroxymuconic 6-semialdehyde dehydrogenase, 4-oxalocrotonate tautomerase, 4-oxalocrotonate decarboxylase, and 2-oxopent-4-enoate hydratase activities, but no 2-hydroxymuconic 6-semialdehyde hydrolase activity. These enzymes involved in 4-amino-3-hydroxybenzoate metabolism were purified and characterized. When 2-hydroxymuconic 6-semialdehyde was used as substrate in a reaction mixture containing NAD(+) and cell extracts from 4-amino-3-hydroxybenzoate-grown cells, 4-oxalocrotonic acid, 2-oxopent-4-enoic acid, and 4-hydroxy-2-oxovaleric acid were identified as intermediates, and pyruvic acid was identified as the final product. A complete pathway for the metabolism of 4-amino-3-hydroxybenzoic acid in strain 10d is proposed. Strain 10d metabolized 2-hydroxymuconic 6-semialdehyde derived from 4-amino-3-hydroxybenzoic acid via a dehydrogenative route, not via a hydrolytic route. This proposed metabolic pathway differs considerably from the modified meta-cleavage pathway of 2-aminophenol and those previously reported for methyl- and chloro-derivatives. |
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Authors:
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Chika Orii; Shinji Takenaka; Shuichiro Murakami; Kenji Aoki |
Publication Detail:
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Type: Journal Article Date: 2006-11-07 |
Journal Detail:
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Title: Bioscience, biotechnology, and biochemistry Volume: 70 ISSN: 0916-8451 ISO Abbreviation: Biosci. Biotechnol. Biochem. Publication Date: 2006 Nov |
Date Detail:
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Created Date: 2006-11-24 Completed Date: 2007-01-30 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 9205717 Medline TA: Biosci Biotechnol Biochem Country: Japan |
Other Details:
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Languages: eng Pagination: 2653-61 Citation Subset: IM |
Affiliation:
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Division of Science of Biological Resources, Graduate School of Science and Technology, Kobe University, Rokko, Nada-ku, Kobe, Japan. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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4-Aminobenzoic Acid
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analogs & derivatives*,
chemistry,
metabolism Aminophenols / chemistry, metabolism* Bordetella / chemistry, metabolism* Catechols / metabolism Cell Extracts Hydro-Lyases / metabolism Hydroxybenzoic Acids / chemistry, metabolism* Isomerases / isolation & purification, metabolism Mass Spectrometry Molecular Structure Spectrum Analysis |
| Chemical | |
Reg. No./Substance:
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0/4-amino-3-hydroxybenzoic acid; 0/Aminophenols; 0/Catechols; 0/Cell Extracts; 0/Hydroxybenzoic Acids; 120-80-9/catechol; 150-13-0/4-Aminobenzoic Acid; 95-55-6/2-aminophenol; EC 4.2.1.-/Hydro-Lyases; EC 4.2.1.80/2-oxopent-4-enoate hydratase; EC 5.-/4-oxalocrotonate tautomerase; EC 5.-/Isomerases |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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