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Title: Biomimetic Reductive Cleavage of Keto Aryl Ether Bonds by Small‐Molecule Thiols

Authors:
ORCiD logo [1];  [2];  [2];  [2];  [2]; ORCiD logo [3]; ORCiD logo [4]
  1. Department of Biochemistry &, Molecular BiologyMichigan State University 603 Wilson Rd East Lansing Michigan 48824 USA, Department of ChemistryMichigan State University 578 S Shaw Ln East Lansing Michigan 48824 USA, Great Lakes Bioenergy Research CenterMichigan State University 164 Food Safety and Toxicology Building East Lansing Michigan 48824 USA
  2. Department of ChemistryMichigan State University 578 S Shaw Ln East Lansing Michigan 48824 USA
  3. Department of ChemistryMichigan State University 578 S Shaw Ln East Lansing Michigan 48824 USA, Great Lakes Bioenergy Research CenterMichigan State University 164 Food Safety and Toxicology Building East Lansing Michigan 48824 USA
  4. Department of Biochemistry &, Molecular BiologyMichigan State University 603 Wilson Rd East Lansing Michigan 48824 USA, Great Lakes Bioenergy Research CenterMichigan State University 164 Food Safety and Toxicology Building East Lansing Michigan 48824 USA
Publication Date:
Sponsoring Org.:
USDOE Office of Science (SC), Biological and Environmental Research (BER)
OSTI Identifier:
1561328
Grant/Contract Number:  
SC0018409; FC02-07ER64494
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
ChemSusChem
Additional Journal Information:
Journal Name: ChemSusChem Journal Volume: 12 Journal Issue: 21; Journal ID: ISSN 1864-5631
Publisher:
Wiley Blackwell (John Wiley & Sons)
Country of Publication:
Germany
Language:
English

Citation Formats

Klinger, Grace E., Zhou, Yuting, Hao, Pengchao, Robbins, Jacob, Aquilina, Jake M., Jackson, James E., and Hegg, Eric L. Biomimetic Reductive Cleavage of Keto Aryl Ether Bonds by Small‐Molecule Thiols. Germany: N. p., 2019. Web. doi:10.1002/cssc.201901742.
Klinger, Grace E., Zhou, Yuting, Hao, Pengchao, Robbins, Jacob, Aquilina, Jake M., Jackson, James E., & Hegg, Eric L. Biomimetic Reductive Cleavage of Keto Aryl Ether Bonds by Small‐Molecule Thiols. Germany. doi:10.1002/cssc.201901742.
Klinger, Grace E., Zhou, Yuting, Hao, Pengchao, Robbins, Jacob, Aquilina, Jake M., Jackson, James E., and Hegg, Eric L. Wed . "Biomimetic Reductive Cleavage of Keto Aryl Ether Bonds by Small‐Molecule Thiols". Germany. doi:10.1002/cssc.201901742.
@article{osti_1561328,
title = {Biomimetic Reductive Cleavage of Keto Aryl Ether Bonds by Small‐Molecule Thiols},
author = {Klinger, Grace E. and Zhou, Yuting and Hao, Pengchao and Robbins, Jacob and Aquilina, Jake M. and Jackson, James E. and Hegg, Eric L.},
abstractNote = {},
doi = {10.1002/cssc.201901742},
journal = {ChemSusChem},
number = 21,
volume = 12,
place = {Germany},
year = {2019},
month = {9}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
DOI: 10.1002/cssc.201901742

Citation Metrics:
Cited by: 2 works
Citation information provided by
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Works referenced in this record:

Structural and Biochemical Characterization of the Early and Late Enzymes in the Lignin β-Aryl Ether Cleavage Pathway from Sphingobium sp. SYK-6
journal, March 2016

  • Pereira, Jose Henrique; Heins, Richard A.; Gall, Daniel L.
  • Journal of Biological Chemistry, Vol. 291, Issue 19
  • DOI: 10.1074/jbc.M115.700427

Gaussian-3 theory using reduced Mo/ller-Plesset order
journal, March 1999

  • Curtiss, Larry A.; Redfern, Paul C.; Raghavachari, Krishnan
  • The Journal of Chemical Physics, Vol. 110, Issue 10
  • DOI: 10.1063/1.478385

How Alkyl Halide Structure Affects E2 and S N 2 Reaction Barriers: E2 Reactions Are as Sensitive as S N 2 Reactions
journal, January 2014

  • Rablen, Paul R.; McLarney, Brett D.; Karlow, Brandon J.
  • The Journal of Organic Chemistry, Vol. 79, Issue 3
  • DOI: 10.1021/jo4026644

A heterodimeric glutathione S -transferase that stereospecifically breaks lignin's β( R )-aryl ether bond reveals the diversity of bacterial β-etherases
journal, December 2018

  • Kontur, Wayne S.; Olmsted, Charles N.; Yusko, Larissa M.
  • Journal of Biological Chemistry, Vol. 294, Issue 6
  • DOI: 10.1074/jbc.RA118.006548

A Group of Sequence-Related Sphingomonad Enzymes Catalyzes Cleavage of β-Aryl Ether Linkages in Lignin β-Guaiacyl and β-Syringyl Ether Dimers
journal, October 2014

  • Gall, Daniel L.; Ralph, John; Donohue, Timothy J.
  • Environmental Science & Technology, Vol. 48, Issue 20
  • DOI: 10.1021/es503886d

Bright Side of Lignin Depolymerization: Toward New Platform Chemicals
journal, January 2018


Chemical Groups and Structural Characterization of Lignin via Thiol-Mediated Demethylation
journal, December 2013


The electrochemistry of l-cystine and l-cysteine part 2 : Electrosynthesis of l-cysteine at solid electrodes
journal, September 1994

  • Ralph, T. R.; Hitchman, M. L.; Millington, J. P.
  • Journal of Electroanalytical Chemistry, Vol. 375, Issue 1-2
  • DOI: 10.1016/0022-0728(94)03408-7

Wege zur Verwertung von Lignin: Fortschritte in der Biotechnik, der Bioraffination und der Katalyse
journal, June 2016

  • Rinaldi, Roberto; Jastrzebski, Robin; Clough, Matthew T.
  • Angewandte Chemie, Vol. 128, Issue 29
  • DOI: 10.1002/ange.201510351

Structural Basis of Stereospecificity in the Bacterial Enzymatic Cleavage of β-Aryl Ether Bonds in Lignin
journal, December 2015

  • Helmich, Kate E.; Pereira, Jose Henrique; Gall, Daniel L.
  • Journal of Biological Chemistry, Vol. 291, Issue 10
  • DOI: 10.1074/jbc.M115.694307

Mechanistic Studies on a Sulfoxide Transfer Reaction Mediated by Diphenyl Sulfoxide/Triflic Anhydride
journal, January 2012

  • Fascione, Martin A.; Adshead, Sophie J.; Mandal, Pintu K.
  • Chemistry - A European Journal, Vol. 18, Issue 10
  • DOI: 10.1002/chem.201102861

Density Functional Theory Calculation of p K a ’s of Thiols in Aqueous Solution Using Explicit Water Molecules and the Polarizable Continuum Model
journal, June 2016

  • Thapa, Bishnu; Schlegel, H. Bernhard
  • The Journal of Physical Chemistry A, Vol. 120, Issue 28
  • DOI: 10.1021/acs.jpca.6b05040

Novosphingobium aromaticivorans uses a Nu-class glutathione S -transferase as a glutathione lyase in breaking the β-aryl ether bond of lignin
journal, February 2018

  • Kontur, Wayne S.; Bingman, Craig A.; Olmsted, Charles N.
  • Journal of Biological Chemistry, Vol. 293, Issue 14
  • DOI: 10.1074/jbc.RA117.001268

The Effect of the Carbonyl and Related Groups on the Reactivity of Halides in SN2 Reactions
journal, November 1964

  • Bordwell, F. G.; Brannen, W. T.
  • Journal of the American Chemical Society, Vol. 86, Issue 21
  • DOI: 10.1021/ja01075a025

Bacterial catabolism of lignin-derived aromatics: New findings in a recent decade: Update on bacterial lignin catabolism: Bacterial catabolism of lignin-derived aromatics
journal, November 2017

  • Kamimura, Naofumi; Takahashi, Kenji; Mori, Kosuke
  • Environmental Microbiology Reports, Vol. 9, Issue 6
  • DOI: 10.1111/1758-2229.12597

Paving the Way for Lignin Valorisation: Recent Advances in Bioengineering, Biorefining and Catalysis
journal, June 2016

  • Rinaldi, Roberto; Jastrzebski, Robin; Clough, Matthew T.
  • Angewandte Chemie International Edition, Vol. 55, Issue 29
  • DOI: 10.1002/anie.201510351

Lignin Functionalization through Chemical Demethylation: Preparation and Tannin-Like Properties of Demethylated Guaiacyl-Type Synthetic Lignins
journal, May 2017

  • Sawamura, Kaori; Tobimatsu, Yuki; Kamitakahara, Hiroshi
  • ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 6
  • DOI: 10.1021/acssuschemeng.7b00748

Equilibrium deuterium isotope effects on the ionization of thiol acids
journal, September 1971

  • Jencks, William P.; Salvesen, Karin
  • Journal of the American Chemical Society, Vol. 93, Issue 18
  • DOI: 10.1021/ja00747a016

Electrochemical Manufacturing in the Chemical Industry
journal, January 2014


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

  • Picart, Pere; Müller, Christoph; Mottweiler, Jakob
  • ChemSusChem, Vol. 7, Issue 11
  • DOI: 10.1002/cssc.201402465

Rates of thiol-disulfide interchange reactions between mono- and dithiols and Ellman's reagent
journal, January 1977

  • Whitesides, George M.; Lilburn, Jennifer E.; Szajewski, Richard P.
  • The Journal of Organic Chemistry, Vol. 42, Issue 2
  • DOI: 10.1021/jo00422a034

Self-Consistent Reaction Field Model for Aqueous and Nonaqueous Solutions Based on Accurate Polarized Partial Charges
journal, October 2007

  • Marenich, Aleksandr V.; Olson, Ryan M.; Kelly, Casey P.
  • Journal of Chemical Theory and Computation, Vol. 3, Issue 6
  • DOI: 10.1021/ct7001418

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

  • Gall, Daniel L.; Kim, Hoon; Lu, Fachuang
  • Journal of Biological Chemistry, Vol. 289, Issue 12
  • DOI: 10.1074/jbc.M113.536250