2-Naphthoate catabolic pathway in Burkholderia strain JT 1500.
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.
Morawski
B
B
Institute of Organic Chemistry, SFB Biocatalysis, Technical University Graz, Austria.
Eaton
R W
RW
Rossiter
J T
JT
Guoping
S
S
Griengl
H
H
Ribbons
D W
DW
D001673:Biodegradation, Environmental; D019117:Burkholderia / Q000201:enzymology / Q000378:metabolism*; D002244:Carbon / Q000378:metabolism; D008956:Models, Chemical; D009281:Naphthalenes / Q000378:metabolism*; D010101:Oxygen Consumption
D009281:Naphthalenes; D002244:Carbon; C030037:2-naphthoic acid