A Group of Sequence-Related Sphingomonad Enzymes Catalyzes Cleavage of β-Aryl Ether Linkages in Lignin β-Guaiacyl and β-Syringyl Ether Dimers

Gall, Daniel L.; Ralph, John; Donohue, Timothy J.; Noguera, Daniel R.

doi:10.1021/es503886d

Title: A Group of Sequence-Related Sphingomonad Enzymes Catalyzes Cleavage of β-Aryl Ether Linkages in Lignin β-Guaiacyl and β-Syringyl Ether Dimers

Authors:

Gall, Daniel L. ^[1]; Ralph, John ^[2]; Donohue, Timothy J. ^[3]; Noguera, Daniel R. ^[4]

Department of Civil & Environmental Engineering, University of Wisconsin, Madison, Wisconsin 53706, United States, U.S. Department of Energy’s Great Lakes Bioenergy Research Center, Wisconsin Energy Institute, University of Wisconsin, Madison Wisconsin 53726, United States
U.S. Department of Energy’s Great Lakes Bioenergy Research Center, Wisconsin Energy Institute, University of Wisconsin, Madison Wisconsin 53726, United States, Department of Biochemistry, University of Wisconsin, Madison, Wisconsin 53706, United States
U.S. Department of Energy’s Great Lakes Bioenergy Research Center, Wisconsin Energy Institute, University of Wisconsin, Madison Wisconsin 53726, United States, Department of Bacteriology, University of Wisconsin, Madison, Wisconsin 53706, United States
Department of Civil & Environmental Engineering, University of Wisconsin, Madison, Wisconsin 53706, United States, U.S. Department of Energy’s Great Lakes Bioenergy Research Center, Wisconsin Energy Institute, University of Wisconsin, Madison Wisconsin 53726, United States, Environmental Chemistry and Technology Program, University of Wisconsin, Madison, Wisconsin 53706, United States

Publication Date:: Wed Oct 01 00:00:00 EDT 2014

Sponsoring Org.:: USDOE

OSTI Identifier:: 1159113

Grant/Contract Number:: FC02-07ER64494

Resource Type:: Published Article

Journal Name:: Environmental Science and Technology

Additional Journal Information:: Journal Name: Environmental Science and Technology Journal Volume: 48 Journal Issue: 20; Journal ID: ISSN 0013-936X

Publisher:: American Chemical Society

Country of Publication:: United States

Language:: English

Citation Formats


                    Gall, Daniel L., Ralph, John, Donohue, Timothy J., and Noguera, Daniel R. A Group of Sequence-Related Sphingomonad Enzymes Catalyzes Cleavage of β-Aryl Ether Linkages in Lignin β-Guaiacyl and β-Syringyl Ether Dimers.  United States: N. p., 2014. 
Web.  doi:10.1021/es503886d.

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                    Gall, Daniel L., Ralph, John, Donohue, Timothy J., & Noguera, Daniel R. A Group of Sequence-Related Sphingomonad Enzymes Catalyzes Cleavage of β-Aryl Ether Linkages in Lignin β-Guaiacyl and β-Syringyl Ether Dimers.  United States.  https://doi.org/10.1021/es503886d

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                    Gall, Daniel L., Ralph, John, Donohue, Timothy J., and Noguera, Daniel R. Wed .  
"A Group of Sequence-Related Sphingomonad Enzymes Catalyzes Cleavage of β-Aryl Ether Linkages in Lignin β-Guaiacyl and β-Syringyl Ether Dimers".  United States.  https://doi.org/10.1021/es503886d.

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@article{osti_1159113,

  title        = {A Group of Sequence-Related Sphingomonad Enzymes Catalyzes Cleavage of β-Aryl Ether Linkages in Lignin β-Guaiacyl and β-Syringyl Ether Dimers},

  author       = {Gall, Daniel L. and Ralph, John and Donohue, Timothy J. and Noguera, Daniel R.},

  abstractNote = {},

  doi          = {10.1021/es503886d},

  journal      = {Environmental Science and Technology},

  number       = 20,

  volume       = 48,

  place        = {United States},

  year         = {Wed Oct 01 00:00:00 EDT 2014},

  month        = {Wed Oct 01 00:00:00 EDT 2014}

}

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Title: A Group of Sequence-Related Sphingomonad Enzymes Catalyzes Cleavage of β-Aryl Ether Linkages in Lignin β-Guaiacyl and β-Syringyl Ether Dimers

Citation Formats

Guaiacylglycerol and its beta-Guaiacyl Ether. journal, January 1955

Synthesis of 14 C Labeled 3-Methoxy-4-Hydroxy -α-(2-Methoxy-phenoxy)-β-Hydroxypropiophenone, a Lignin Model Compound journal, January 1981

Isolation and Characterization of a Novel Polycyclic Aromatic Hydrocarbon–Degrading Bacterium, Sphingopyxis sp. strain M2R2, Capable of Passive Spreading Motility Through Soil journal, June 2010

Stress-Induced Phenylpropanoid Metabolism journal, July 1995

Lignin modification improves fermentable sugar yields for biofuel production journal, June 2007

Detection and localization of a new enzyme catalyzing the β-aryl ether cleavage in the soil bacterium ( Pseudomonas paucimobilis SYK-6) journal, June 1989

The Marine Isolate Novosphingobium sp. PP1Y Shows Specific Adaptation to Use the Aromatic Fraction of Fuels as the Sole Carbon and Energy Source journal, January 2011

Specific degradation ofβ-aryl ether linkage in synthetic lignin (dehydrogenative polymerizate) by bacterial enzymes ofSphingomonas paucimobilis SYK-6 produced in recombinantEscherichia coli journal, October 2002

Autoprocessing of the Vibrio cholerae RTX toxin by the cysteine protease domain journal, April 2007

The Erythro/Threo Ratio of β-O-4 Structures as an Important Structural Characteristic of Lignin. Part 2. Changes in Erythro/Threo (E/T) Ratio of β-O-4 Structures during Delignification Reactions journal, June 2002

Structure and Function of the Xenobiotic Substrate Binding Site of a Glutathione S-Transferase as Revealed by X-ray Crystallographic Analysis of Product Complexes with the Diastereomers of 9-(S-Glutathionyl)-10-hydroxy-9,10-dihydrophenanthrene journal, February 1994

The Catalytic Valorization of Lignin for the Production of Renewable Chemicals journal, June 2010

Are Lignins Optically Active? journal, August 1999

Characterization of the Third Glutathione S -Transferase Gene Involved in Enantioselective Cleavage of the β-Aryl Ether by Sphingobium sp. Strain SYK-6 journal, December 2011

Proposal of the genus Sphingomonas sensu stricto and three new genera, Sphingobium, Novosphingobium and Sphingopyxis, on the basis of phylogenetic and chemotaxonomic analyses. journal, July 2001

Characterization of the Cα-Dehydrogenase Gene Involved in the Cleavage of β-Aryl Ether by Pseudomonas paucimobilis journal, January 1993

Proof of the presence of racemic forms of arylglycerol-Β-aryl ether structure in lignin: studies on the stereo structure of lignin by ozonation journal, October 2000

Basic local alignment search tool journal, October 1990

Lignin: Occurrence, Biogenesis and Biodegradation journal, June 1990

Advances in modifying lignin for enhanced biofuel production journal, June 2010

Cloning and sequencing of the gene for a Pseudomonas paucimobilis enzyme that cleaves beta-aryl ether. journal, January 1991

A combined approach to improving large-scale production of tobacco etch virus protease journal, September 2007

Mechanistic and structural insights into the proteolytic activation of Vibrio cholerae MARTX toxin journal, May 2009

Complete Genome Sequence of Sphingobium sp. Strain SYK-6, a Degrader of Lignin-Derived Biaryls and Monoaryls journal, December 2011

Identification of Three Alcohol Dehydrogenase Genes Involved in the Stereospecific Catabolism of Arylglycerol- -Aryl Ether by Sphingobium sp. Strain SYK-6 journal, June 2009

Convenient synthesis of chiral lignin model compounds via optical resolution: four stereoisomers of guaiacylglycerol-β-guaiacyl ether and both enantiomers of 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)-propan-1-one (erone) journal, February 2012

Structural and Molecular Mechanism for Autoprocessing of MARTX Toxin of Vibrio cholerae at Multiple Sites journal, September 2009

Lignin chemistry?past, present and future journal, January 1977

Structure of an insect δ-class glutathione S -transferase from a DDT-resistant strain of the malaria vector Anopheles gambiae journal, November 2003

From Gene Towards Selective Biomass Valorization: Bacterial β-Etherases with Catalytic Activity on Lignin-Like Polymers journal, September 2014

Genetic and Biochemical Investigations on Bacterial Catabolic Pathways for Lignin-Derived Aromatic Compounds journal, January 2007

Roles of the Enantioselective Glutathione S-Transferases in Cleavage of -Aryl Ether journal, March 2003

A bacterial enzyme degrading the model lignin compound β-etherase is a member of the glutathione- S -transferase superfamily journal, May 1993

Biosynthesis and Constitution of Lignin journal, April 1959

The emerging role for bacteria in lignin degradation and bio-product formation journal, June 2011

Isolation and characterization of phenanthrene-degrading Sphingomonas paucimobilis strain ZX4 journal, October 2005

Stereochemical Features of Glutathione-dependent Enzymes in the Sphingobium sp. Strain SYK-6 β-Aryl Etherase Pathway journal, February 2014

De Novo Sequencing and Assembly of the Whole Genome of Novosphingobium sp. Strain PP1Y journal, June 2011

Erythro/threo ratio ofβ-O-4 structures as an important structural characteristic of lignin. I: Improvement of ozonation method for the quantitative analysis of lignin side-chain structure journal, June 2002

Guaiacylglycerol and its beta-Guaiacyl Ether.
journal, January 1955

Synthesis of ¹⁴ C Labeled 3-Methoxy-4-Hydroxy -α-(2-Methoxy-phenoxy)-β-Hydroxypropiophenone, a Lignin Model Compound
journal, January 1981

Isolation and Characterization of a Novel Polycyclic Aromatic Hydrocarbon–Degrading Bacterium, Sphingopyxis sp. strain M2R2, Capable of Passive Spreading Motility Through Soil
journal, June 2010

Stress-Induced Phenylpropanoid Metabolism
journal, July 1995

Lignin modification improves fermentable sugar yields for biofuel production
journal, June 2007

Detection and localization of a new enzyme catalyzing the β-aryl ether cleavage in the soil bacterium ( Pseudomonas paucimobilis SYK-6)
journal, June 1989

The Marine Isolate Novosphingobium sp. PP1Y Shows Specific Adaptation to Use the Aromatic Fraction of Fuels as the Sole Carbon and Energy Source
journal, January 2011

Specific degradation ofβ-aryl ether linkage in synthetic lignin (dehydrogenative polymerizate) by bacterial enzymes ofSphingomonas paucimobilis SYK-6 produced in recombinantEscherichia coli
journal, October 2002

Autoprocessing of the Vibrio cholerae RTX toxin by the cysteine protease domain
journal, April 2007

The Erythro/Threo Ratio of β-O-4 Structures as an Important Structural Characteristic of Lignin. Part 2. Changes in Erythro/Threo (E/T) Ratio of β-O-4 Structures during Delignification Reactions
journal, June 2002

Structure and Function of the Xenobiotic Substrate Binding Site of a Glutathione S-Transferase as Revealed by X-ray Crystallographic Analysis of Product Complexes with the Diastereomers of 9-(S-Glutathionyl)-10-hydroxy-9,10-dihydrophenanthrene
journal, February 1994

The Catalytic Valorization of Lignin for the Production of Renewable Chemicals
journal, June 2010

Are Lignins Optically Active?
journal, August 1999

Characterization of the Third Glutathione S -Transferase Gene Involved in Enantioselective Cleavage of the β-Aryl Ether by Sphingobium sp. Strain SYK-6
journal, December 2011

Proposal of the genus Sphingomonas sensu stricto and three new genera, Sphingobium, Novosphingobium and Sphingopyxis, on the basis of phylogenetic and chemotaxonomic analyses.
journal, July 2001

Characterization of the Cα-Dehydrogenase Gene Involved in the Cleavage of β-Aryl Ether by Pseudomonas paucimobilis
journal, January 1993

Proof of the presence of racemic forms of arylglycerol-Β-aryl ether structure in lignin: studies on the stereo structure of lignin by ozonation
journal, October 2000

Basic local alignment search tool
journal, October 1990

Lignin: Occurrence, Biogenesis and Biodegradation
journal, June 1990

Advances in modifying lignin for enhanced biofuel production
journal, June 2010

Cloning and sequencing of the gene for a Pseudomonas paucimobilis enzyme that cleaves beta-aryl ether.
journal, January 1991

A combined approach to improving large-scale production of tobacco etch virus protease
journal, September 2007

Mechanistic and structural insights into the proteolytic activation of Vibrio cholerae MARTX toxin
journal, May 2009

Complete Genome Sequence of Sphingobium sp. Strain SYK-6, a Degrader of Lignin-Derived Biaryls and Monoaryls
journal, December 2011

Identification of Three Alcohol Dehydrogenase Genes Involved in the Stereospecific Catabolism of Arylglycerol- -Aryl Ether by Sphingobium sp. Strain SYK-6
journal, June 2009

Convenient synthesis of chiral lignin model compounds via optical resolution: four stereoisomers of guaiacylglycerol-β-guaiacyl ether and both enantiomers of 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)-propan-1-one (erone)
journal, February 2012

Structural and Molecular Mechanism for Autoprocessing of MARTX Toxin of Vibrio cholerae at Multiple Sites
journal, September 2009

Lignin chemistry?past, present and future
journal, January 1977

Structure of an insect δ-class glutathione S -transferase from a DDT-resistant strain of the malaria vector Anopheles gambiae
journal, November 2003

From Gene Towards Selective Biomass Valorization: Bacterial β-Etherases with Catalytic Activity on Lignin-Like Polymers
journal, September 2014

Genetic and Biochemical Investigations on Bacterial Catabolic Pathways for Lignin-Derived Aromatic Compounds
journal, January 2007

Roles of the Enantioselective Glutathione S-Transferases in Cleavage of -Aryl Ether
journal, March 2003

A bacterial enzyme degrading the model lignin compound β-etherase is a member of the glutathione- S -transferase superfamily
journal, May 1993

Biosynthesis and Constitution of Lignin
journal, April 1959

The emerging role for bacteria in lignin degradation and bio-product formation
journal, June 2011

Isolation and characterization of phenanthrene-degrading Sphingomonas paucimobilis strain ZX4
journal, October 2005

Stereochemical Features of Glutathione-dependent Enzymes in the Sphingobium sp. Strain SYK-6 β-Aryl Etherase Pathway
journal, February 2014

De Novo Sequencing and Assembly of the Whole Genome of Novosphingobium sp. Strain PP1Y
journal, June 2011

Erythro/threo ratio ofβ-O-4 structures as an important structural characteristic of lignin. I: Improvement of ozonation method for the quantitative analysis of lignin side-chain structure
journal, June 2002