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Metabolism of 4-amino-3-hydroxybenzoic Acid by Bordetella Sp. Strain 10d: A Different Modified Meta-Cleavage Pathway for 2-aminophenols

Metabolism of 4-amino-3-hydroxybenzoic Acid by Bordetella Sp. Strain 10d: A Different Modified Meta-Cleavage Pathway for 2-aminophenols

Chika Orii, Shinji Takenaka, Shuichiro Murakami, Kenji Aoki

Biosci Biotechnol Biochem. 2006 Nov;70(11):2653-61.

PMID: 17090920

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP118062058	2,3,4-Trimethoxyphenylboronic acid		118062-05-8	Price
AP182163968	3,4,5-Trimethoxyphenylboronic acid		182163-96-8	Price

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