Document Detail


Metabolism of 4-amino-3-hydroxybenzoic acid by Bordetella sp. strain 10d: A different modified meta-cleavage pathway for 2-aminophenols.
MedLine Citation:
PMID:  17090920     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
Chika Orii; Shinji Takenaka; Shuichiro Murakami; Kenji Aoki
Publication Detail:
Type:  Journal Article     Date:  2006-11-07
Journal Detail:
Title:  Bioscience, biotechnology, and biochemistry     Volume:  70     ISSN:  0916-8451     ISO Abbreviation:  Biosci. Biotechnol. Biochem.     Publication Date:  2006 Nov 
Date Detail:
Created Date:  2006-11-24     Completed Date:  2007-01-30     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9205717     Medline TA:  Biosci Biotechnol Biochem     Country:  Japan    
Other Details:
Languages:  eng     Pagination:  2653-61     Citation Subset:  IM    
Affiliation:
Division of Science of Biological Resources, Graduate School of Science and Technology, Kobe University, Rokko, Nada-ku, Kobe, Japan.
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MeSH Terms
Descriptor/Qualifier:
4-Aminobenzoic Acid / 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:
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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