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Applied and Environmental Microbiology, May 2003, p. 2786-2793, Vol. 69, No. 5
0099-2240/03/$08.00+0     DOI: 10.1128/AEM.69.5.2786-2793.2003
Copyright © 2003, American Society for Microbiology. All Rights Reserved.

Bacterial Conversion of Hydroxylamino Aromatic Compounds by both Lyase and Mutase Enzymes Involves Intramolecular Transfer of Hydroxyl Groups

Lloyd J. Nadeau,¹ Zhongqi He,² and Jim C. Spain^1*

Air Force Research Laboratory, Tyndall Air Force Base, Florida 32403,¹ USDA-ARS/New England Plant, Soil, and Water Laboratory, University of Maine, Orono, Maine 04469²

Received 19 September 2002/ Accepted 18 February 2003

Hydroxylamino aromatic compounds are converted to either the corresponding aminophenols or protocatechuate during the bacterial degradation of nitroaromatic compounds. The origin of the hydroxyl group of the products could be the substrate itself (intramolecular transfer mechanism) or the solvent water (intermolecular transfer mechanism). The conversion of hydroxylaminobenzene to 2-aminophenol catalyzed by a mutase from Pseudomonas pseudoalcaligenes JS45 proceeds by an intramolecular hydroxyl transfer. The conversions of hydroxylaminobenzene to 2- and 4-aminophenol by a mutase from Ralstonia eutropha JMP134 and to 4-hydroxylaminobenzoate to protocatechuate by a lyase from Comamonas acidovorans NBA-10 and Pseudomonas sp. strain 4NT were proposed, but not experimentally proved, to proceed by the intermolecular transfer mechanism. GC-MS analysis of the reaction products formed in H₂¹⁸O did not indicate any ¹⁸O-label incorporation during the conversion of hydroxylaminobenzene to 2- and 4-aminophenols catalyzed by the mutase from R. eutropha JMP134. During the conversion of 4-hydroxylaminobenzoate catalyzed by the hydroxylaminolyase from Pseudomonas sp. strain 4NT, only one of the two hydroxyl groups in the product, protocatechuate, was ¹⁸O labeled. The other hydroxyl group in the product must have come from the substrate. The mutase in strain JS45 converted 4-hydroxylaminobenzoate to 4-amino-3-hydroxybenzoate, and the lyase in Pseudomonas strain 4NT converted hydroxylaminobenzene to aniline and 2-aminophenol but not to catechol. The results indicate that all three types of enzyme-catalyzed rearrangements of hydroxylamino aromatic compounds proceed via intramolecular transfer of hydroxyl groups.

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* Corresponding author. Mailing address: AFRL/MLQL, 139 Barnes Dr., Ste. 2, Tyndall AFB, FL 32403. Phone: (850) 283-6058. Fax: (850) 283-6090. E-mail: jim.spain{at}tyndall.af.mil.

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Applied and Environmental Microbiology, May 2003, p. 2786-2793, Vol. 69, No. 5
0099-2240/03/$08.00+0     DOI: 10.1128/AEM.69.5.2786-2793.2003
Copyright © 2003, American Society for Microbiology. All Rights Reserved.

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