title: 2-Naphthoate catabolic pathway in Burkholderia strain JT 1500.
abstract: Burkholderia strain (JT 1500), able to use 2-naphthoate as the sole source of carbon, was isolated from soil. On the basis of growth characteristics, oxygen uptake experiments, enzyme assays, and detection of intermediates, a degradation pathway of 2-naphthoate is proposed. The features of this pathway are convergent with those for phenanthrene. We propose a pathway for the conversion of 2-naphthoate to 1 mol (each) of pyruvate, succinate, and acetyl coenzyme A and 2 mol of CO2. During growth in the presence of 2-naphthoate, six metabolites were detected by thin-layer chromatography, high-performance liquid chromatography, and spectroscopy. 1-Hydroxy-2-naphthoate accumulated in the culture broth during growth on 2-naphthoate. Also, the formation of 2'-carboxybenzalpyruvate, phthalaldehydate, phthalate, protocatechuate, and beta-carboxy-cis,cis-muconic acid was demonstrated. (1R,2S)-cis-1,2-Dihydro-1,2-dihydroxy-2-naphthoate was thus considered an intermediate between 2-naphthoate and 1-hydroxy-2-naphthoate, but it was not transformed by whole cells or their extracts. We conclude that this diol is not responsible for the formation of 1-hydroxy-2-naphthoate from 2-naphthoate but that one of the other three diastereomers is not eliminated as a potential intermediate for a dehydration reaction.
authors.affiliation: Institute of Organic Chemistry, SFB Biocatalysis, Technical University Graz, Austria.
authors.forename: B
authors.initials: B
authors.lastname: Morawski
authors.forename: R W
authors.initials: RW
authors.lastname: Eaton
authors.forename: J T
authors.initials: JT
authors.lastname: Rossiter
authors.forename: S
authors.initials: S
authors.lastname: Guoping
authors.forename: H
authors.initials: H
authors.lastname: Griengl
authors.forename: D W
authors.initials: DW
authors.lastname: Ribbons
mesh_terms: D001673:Biodegradation, Environmental; D019117:Burkholderia / Q000201:enzymology / Q000378:metabolism*; D002244:Carbon / Q000378:metabolism; D008956:Models, Chemical; D009281:Naphthalenes / Q000378:metabolism*; D010101:Oxygen Consumption
chemical_list: D009281:Naphthalenes; D002244:Carbon; C030037:2-naphthoic acid