Metabolism of 4-Amino-3-hydroxybenzoic Acid by Bordetella sp. Strain 10d: A Different Modified Meta-Cleavage Pathway for 2-Aminophenols

• ORII Chika

  Division of Science of Biological Resources, Graduate School of Science and Technology, Kobe University

• TAKENAKA Shinji

  Department of Biofunctional Chemistry, Faculty of Agriculture, Kobe University

• MURAKAMI Shuichiro

  Department of Biofunctional Chemistry, Faculty of Agriculture, Kobe University

• AOKI Kenji

  Department of Biofunctional Chemistry, Faculty of Agriculture, Kobe University

Bibliographic Information

Other Title

• Metabolism of 4-Amino-3-hydroxybenzoic Acid by<i>Bordetella</i>sp. Strain 10d: A Different Modified<i>Meta</i>-Cleavage Pathway for 2-Aminophenols

Abstract

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.

Journal

• Bioscience, Biotechnology, and Biochemistry

  Bioscience, Biotechnology, and Biochemistry 70 (11), 2653-2661, 2006

  Japan Society for Bioscience, Biotechnology, and Agrochemistry

Keywords

• <I>Bordetella</I>
• 4-amino-3-hydroxybenzoic acid
• 4-amino-3-hydroxybenzoate 2,3-dioxygenase
• 2-amino-5-carboxymuconic 6-semialdehyde deaminase
• modified <I>meta</I>-cleavage pathway

Details

• CRID: 1390282681454297088
• NII Article ID: 10018524739
• NII Book ID: AA10824164
• DOI: 10.1271/bbb.60264
• ISSN: 13476947
• ISSN: 09168451
• NDL BIB ID: 8560403
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I8560403
• Web Site: http://www.tandfonline.com/doi/pdf/10.1271/bbb.60264
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
• Abstract License Flag: Disallowed