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:
-
- Georgia Inst. of Technology, Atlanta, GA (United States)
- 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)
- OSTI Identifier:
- 1376559
- Grant/Contract Number:
- AC05-00OR22725
- Resource Type:
- Journal Article: 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. https://doi.org/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. https://doi.org/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},
url = {https://www.osti.gov/biblio/1376559},
journal = {Journal of Molecular Catalysis B: Enzymatic},
issn = {1381-1177},
number = ,
volume = 119,
place = {United States},
year = {2015},
month = {6}
}
Search WorldCat to find libraries that may hold this journalWeb of Science
Works referencing / citing this record:
Laccase-catalyzed green synthesis and cytotoxic activity of novel pyrimidobenzothiazoles and catechol thioethers
journal, January 2017
- Abdel-Mohsen, H. T.; Conrad, J.; Harms, K.
- RSC Advances, Vol. 7, Issue 28
Laccase-catalyzed green synthesis and cytotoxic activity of novel pyrimidobenzothiazoles and catechol thioethers
journal, January 2017
- Abdel-Mohsen, H. T.; Conrad, J.; Harms, K.
- RSC Advances, Vol. 7, Issue 28
Laccase catalysis for the synthesis of bioactive compounds
journal, November 2016
- Kudanga, Tukayi; Nemadziva, Blessing; Le Roes-Hill, Marilize
- Applied Microbiology and Biotechnology, Vol. 101, Issue 1
Efficient and sustainable laccase-catalyzed iodination of p -substituted phenols using KI as iodine source and aerial O 2 as oxidant
journal, January 2019
- Sdahl, Mark; Conrad, Jürgen; Braunberger, Christina
- RSC Advances, Vol. 9, Issue 34
The development of CotA mediator cocktail system for dyes decolorization
journal, March 2018
- Luo, S.; Xie, T.; Liu, Z.
- Journal of Applied Microbiology, Vol. 124, Issue 5