Evidence for the role of 2-hydroxychromene-2-carboxylate isomerase in the degradation of anthracene by Sphingomonas yanoikuyae B1

• Published in: FEMS microbiology letters Vol. 153; no. 2; pp. 479 - 484
• Main Authors: Kim, Eungbin, Zylstra, Gerben J, Freeman, James P, Heinze, Thomas M, Deck, Joanna, Cerniglia, Carl E
• Format: Journal Article
• Language: English
• Published: Oxford, UK Blackwell Publishing Ltd 01.08.1997; Oxford University Press
• Subjects: Anthracene; Anthracenes - metabolism; Biodegradation; Biodegradation, Environmental; Coumarins - metabolism; Degradation; Gram-Negative Aerobic Bacteria - enzymology; Gram-Negative Aerobic Bacteria - metabolism; High performance liquid chromatography; Intramolecular Oxidoreductases; Isomerases - metabolism; Liquid chromatography; Metabolites; Microbiology; Models, Chemical; Mutants; Naphthalene; Naphthalenes - metabolism; NMR; Nuclear magnetic resonance; Organic chemistry; Polycyclic aromatic hydrocarbon; Spectrometry; Sphingomonas; Biodegradation; Anthracene; Polycyclic aromatic hydrocarbon
• ISSN: 0378-1097; 1574-6968
• DOI: 10.1111/j.1574-6968.1997.tb12613.x

Abstract Sphingomonas yanoikuyae B1 is extremely versatile in its catabolic ability. An insertional mutant strain, S. yanoikuyae EK504, which is unable to grow on naphthalene due to the loss of 2-hydroxychromene-2-carboxylate isomerase activity, was utilized to investigate the role of this enzyme in the degradation of anthracene by S. yanoikuyae B1. Although EK504 is unable to grow on anthracene, this strain could transform anthracene to some extent. A metabolite in the degradation of anthracene by EK504 was isolated by high-pressure liquid chromatography (HPLC) and was identified as 6,7-benzocoumarin by UV-visible, gas-chromatographic, HPLC/mass-spectrometric, and 1H nuclear magnetic resonance spectral techniques. The identification of 6,7-benzocoumarin provides direct chemical and genetic evidence for the involvement of nahD in the degradation of anthracene by S. yanoikuyae B1.