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Title: Laccase-catalyzed synthesis of 2,3-ethylenedithio-1,4-quinones

Abstract

Laccases (benzenediol:oxygen oxidoreductase EC 1.10.3.2) are part of a family of multicopper oxidases. These environmentally friendly enzymes require O 2 as their only co-substrate and produce H 2O as their sole by-product. As a result, they have acquired increasing use in biotechnological applications, particularly in the field of organic synthesis. In the current study, laccases have been employed to successfully couple 1,2-ethanedithiol to various substituted hydroquinones to produce novel 2,3-ethylenedithio-1,4-quinones in good yields via an oxidation–addition–oxidation–addition–oxidation mechanism. The reactions proceeded in one-pot under mild conditions (room temperature, pH 5.0). This study further supports the use of laccases as green tools in organic chemistry. Furthermore, it provides evidence that laccase-catalyzed cross-coupling reactions involving small thiols are possible, in spite of research that suggests small thiols are potent inhibitors of laccases.

Authors:
 [1];  [2]
  1. Georgia Inst. of Technology, Atlanta, GA (United States)
  2. Georgia Inst. of Technology, Atlanta, GA (United States); Univ. of Tennessee, Knoxville, TN (United States)
Publication Date:
Research Org.:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Biological and Environmental Research (BER) (SC-23)
OSTI Identifier:
1376559
Grant/Contract Number:  
AC05-00OR22725
Resource Type:
Accepted Manuscript
Journal Name:
Journal of Molecular Catalysis B: Enzymatic
Additional Journal Information:
Journal Volume: 119; Journal ID: ISSN 1381-1177
Publisher:
Elsevier
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Cannatelli, Mark D., and Ragauskas, Arthur J. Laccase-catalyzed synthesis of 2,3-ethylenedithio-1,4-quinones. United States: N. p., 2015. Web. doi:10.1016/j.molcatb.2015.05.016.
Cannatelli, Mark D., & Ragauskas, Arthur J. Laccase-catalyzed synthesis of 2,3-ethylenedithio-1,4-quinones. United States. doi:10.1016/j.molcatb.2015.05.016.
Cannatelli, Mark D., and Ragauskas, Arthur J. Fri . "Laccase-catalyzed synthesis of 2,3-ethylenedithio-1,4-quinones". United States. doi:10.1016/j.molcatb.2015.05.016. https://www.osti.gov/servlets/purl/1376559.
@article{osti_1376559,
title = {Laccase-catalyzed synthesis of 2,3-ethylenedithio-1,4-quinones},
author = {Cannatelli, Mark D. and Ragauskas, Arthur J.},
abstractNote = {Laccases (benzenediol:oxygen oxidoreductase EC 1.10.3.2) are part of a family of multicopper oxidases. These environmentally friendly enzymes require O2 as their only co-substrate and produce H2O as their sole by-product. As a result, they have acquired increasing use in biotechnological applications, particularly in the field of organic synthesis. In the current study, laccases have been employed to successfully couple 1,2-ethanedithiol to various substituted hydroquinones to produce novel 2,3-ethylenedithio-1,4-quinones in good yields via an oxidation–addition–oxidation–addition–oxidation mechanism. The reactions proceeded in one-pot under mild conditions (room temperature, pH 5.0). This study further supports the use of laccases as green tools in organic chemistry. Furthermore, it provides evidence that laccase-catalyzed cross-coupling reactions involving small thiols are possible, in spite of research that suggests small thiols are potent inhibitors of laccases.},
doi = {10.1016/j.molcatb.2015.05.016},
journal = {Journal of Molecular Catalysis B: Enzymatic},
number = ,
volume = 119,
place = {United States},
year = {2015},
month = {6}
}

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Cited by: 11 works
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