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

Eungbin Kim; Gerben J. Zylstra; James P. Freeman; Thomas M. Heinze; Joanna Deck; Carl E. Cerniglia

doi:10.1016/S0378-1097(97)00292-9

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

Eungbin Kim, Gerben J. Zylstra, James P. Freeman, Thomas M. Heinze, Joanna Deck, Carl E. Cerniglia

School of Environmental and Biological Sciences, Biochemistry & Microbiology

Research output: Contribution to journal › Article › peer-review

26 Scopus citations

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.

Original language	English (US)
Pages (from-to)	479-484
Number of pages	6
Journal	FEMS Microbiology Letters
Volume	153
Issue number	2
DOIs	https://doi.org/10.1016/S0378-1097(97)00292-9
State	Published - Aug 15 1997

All Science Journal Classification (ASJC) codes

Microbiology
Molecular Biology
Genetics

Keywords

Anthracene
Biodegradation
Polycyclic aromatic hydrocarbon
Sphingomonas

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10.1016/S0378-1097(97)00292-9

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

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.",

keywords = "Anthracene, Biodegradation, Polycyclic aromatic hydrocarbon, Sphingomonas",

author = "Eungbin Kim and Zylstra, {Gerben J.} and Freeman, {James P.} and Heinze, {Thomas M.} and Joanna Deck and Cerniglia, {Carl E.}",

note = "Funding Information: This research was supported in part by an appointment to the Postgraduate Research Program at the National Center for Toxicological Research administered by the Oak Ridge Institute for Science and Education through an interagency agreement between the U.S. Department of Energy and the U.S. Food and Drug Administration and by a grant from the Electric Power Research Institute. G.J.Z. is the recipient of a Young Investigator Award from the National Science Foundation. We thank Kay L. Shuttleworth and Jack Lay for critical reading of the manuscript and Kim Otwell for graphic illustrations. ",

year = "1997",

month = aug,

day = "15",

doi = "10.1016/S0378-1097(97)00292-9",

language = "English (US)",

volume = "153",

pages = "479--484",

journal = "FEMS Microbiology Letters",

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T1 - Evidence for the role of 2-hydroxychromene-2-carboxylate isomerase in the degradation of anthracene by Sphingomonas yanoikuyae B1

AU - Kim, Eungbin

AU - Zylstra, Gerben J.

AU - Freeman, James P.

AU - Heinze, Thomas M.

AU - Deck, Joanna

AU - Cerniglia, Carl E.

N1 - Funding Information: This research was supported in part by an appointment to the Postgraduate Research Program at the National Center for Toxicological Research administered by the Oak Ridge Institute for Science and Education through an interagency agreement between the U.S. Department of Energy and the U.S. Food and Drug Administration and by a grant from the Electric Power Research Institute. G.J.Z. is the recipient of a Young Investigator Award from the National Science Foundation. We thank Kay L. Shuttleworth and Jack Lay for critical reading of the manuscript and Kim Otwell for graphic illustrations.

PY - 1997/8/15

Y1 - 1997/8/15

N2 - 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.

AB - 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.

KW - Anthracene

KW - Biodegradation

KW - Polycyclic aromatic hydrocarbon

KW - Sphingomonas

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

Abstract

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