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

Cannatelli, Mark D.; Ragauskas, Arthur J.

doi:10.1016/j.molcatb.2015.05.016

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

Journal Article · Fri Jun 05 04:00:00 UTC 2015 · Journal of Molecular Catalysis B: Enzymatic

DOI: https://doi.org/10.1016/j.molcatb.2015.05.016 · OSTI ID:1376559

Cannatelli, Mark D. ^[1]; Ragauskas, Arthur J. ^[2]

Georgia Inst. of Technology, Atlanta, GA (United States)
Georgia Inst. of Technology, Atlanta, GA (United States); Univ. of Tennessee, Knoxville, TN (United States)

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.

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Research Organization:: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Biological and Environmental Research (BER) (SC-23)

Grant/Contract Number:: AC05-00OR22725

OSTI ID:: 1376559

Journal Information:: Journal of Molecular Catalysis B: Enzymatic, Journal Name: Journal of Molecular Catalysis B: Enzymatic Vol. 119; ISSN 1381-1177

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

References (29)

Synthetic Applications of Laccase in Green Chemistry Witayakran, Suteera; Ragauskas, Arthur J. Advanced Synthesis & Catalysis, Vol. 351, Issue 9 https://doi.org/10.1002/adsc.200800775	journal	June 2009
Laccase and Laccase-Mediated Systems in the Synthesis of Organic Compounds Mogharabi, Mehdi; Faramarzi, Mohammad Ali Advanced Synthesis & Catalysis, Vol. 356, Issue 5 https://doi.org/10.1002/adsc.201300960	journal	February 2014
Laccase-Catalyzed CS and CC Coupling for a One-Pot Synthesis of 1,4-Naphthoquinone Sulfides and 1,4-Naphthoquinone Sulfide Dimers Wellington, Kevin W.; Gordon, Gregory E. R.; Ndlovu, Lindelani A. ChemCatChem, Vol. 5, Issue 6 https://doi.org/10.1002/cctc.201200606	journal	March 2013
First description of a laccase-like enzyme in soil algae Otto, Benjamin; Schlosser, Dietmar; Reisser, Werner Archives of Microbiology, Vol. 192, Issue 9 https://doi.org/10.1007/s00203-010-0603-7	journal	July 2010
Laccase enzyme catalysed efficient synthesis of 3-Substituted-1,2,4-triazoto(4,3-b)(4,1,2)benzothiadiazine-8-ones Bhalerao, Uday T.; Muralikrishna, Chivukula; Rani, Bonala Radha Tetrahedron, Vol. 50, Issue 13 https://doi.org/10.1016/S0040-4020(01)89677-0	journal	March 1994
Laccase activity tests and laccase inhibitors Johannes, Christian; Majcherczyk, Andrzej Journal of Biotechnology, Vol. 78, Issue 2 https://doi.org/10.1016/S0168-1656(00)00208-X	journal	March 2000
Synthesis and biological evaluation of novel 1,4-naphthoquinone derivatives as antibacterial and antiviral agents Tandon, Vishnu K.; Yadav, Dharmendra B.; Singh, Ravindra V. Bioorganic & Medicinal Chemistry Letters, Vol. 15, Issue 14 https://doi.org/10.1016/j.bmcl.2005.04.075	journal	July 2005
Laccase-catalyzed α-arylation of benzoylacetonitrile with substituted hydroquinones Cannatelli, Mark D.; Ragauskas, Arthur J. Chemical Engineering Research and Design, Vol. 97 https://doi.org/10.1016/j.cherd.2014.08.021	journal	May 2015
Synthesis and biological activity of derivatives of the marine quinone avarone Božić, Tatjana; Novaković, Irena; Gašić, Miroslav J. European Journal of Medicinal Chemistry, Vol. 45, Issue 3 https://doi.org/10.1016/j.ejmech.2009.11.033	journal	March 2010
Laccase-induced cross-coupling of 4-aminobenzoic acid with para-dihydroxylated compounds 2,5-dihydroxy-N-(2-hydroxyethyl)-benzamide and 2,5-dihydroxybenzoic acid methyl ester Manda, Katrin; Hammer, Elke; Mikolasch, Annett Journal of Molecular Catalysis B: Enzymatic, Vol. 35, Issue 4-6 https://doi.org/10.1016/j.molcatb.2005.06.001	journal	September 2005
Nuclear amination catalyzed by fungal laccases: Comparison of laccase catalyzed amination with known chemical routes to aminoquinones Niedermeyer, Timo H. J.; Lalk, Michael Journal of Molecular Catalysis B: Enzymatic, Vol. 45, Issue 3-4 https://doi.org/10.1016/j.molcatb.2006.12.006	journal	April 2007
Derivatization of amino acids by fungal laccases: Comparison of enzymatic and chemical methods Hahn, Veronika; Mikolasch, Annett; Manda, Katrin Journal of Molecular Catalysis B: Enzymatic, Vol. 60, Issue 1-2 https://doi.org/10.1016/j.molcatb.2009.04.002	journal	September 2009
Preparation and use of cross-linked enzyme aggregates (CLEAs) of laccases Matijošytė, Inga; Arends, Isabel W. C. E.; de Vries, Simon Journal of Molecular Catalysis B: Enzymatic, Vol. 62, Issue 2 https://doi.org/10.1016/j.molcatb.2009.09.019	journal	February 2010
Structure–function relationship among bacterial, fungal and plant laccases Dwivedi, Upendra N.; Singh, Priyanka; Pandey, Veda P. Journal of Molecular Catalysis B: Enzymatic, Vol. 68, Issue 2 https://doi.org/10.1016/j.molcatb.2010.11.002	journal	February 2011
First time reported enzymatic synthesis of new series of quinoxalines—A green approach Kidwai, Mazaahir; Jain, Arti; Sharma, Abha Journal of Molecular Catalysis B: Enzymatic, Vol. 74, Issue 3-4 https://doi.org/10.1016/j.molcatb.2011.11.002	journal	February 2012
Laccases: blue enzymes for green chemistry Riva, Sergio Trends in Biotechnology, Vol. 24, Issue 5 https://doi.org/10.1016/j.tibtech.2006.03.006	journal	May 2006
Synthesis of Naphthoquinones for Studies of the Inhibition of Enzyme Systems Fieser, Louis F.; Brown, Russell H. Journal of the American Chemical Society, Vol. 71, Issue 11 https://doi.org/10.1021/ja01179a009	journal	November 1949
Laccase-Catalyzed Domino Reaction between Catechols and 6-Substituted 1,2,3,4-Tetrahydro-4-oxo-2-thioxo-5-pyrimidinecarbonitriles for the Synthesis of Pyrimidobenzothiazole Derivatives Abdel-Mohsen, Heba T.; Conrad, Jürgen; Beifuss, Uwe The Journal of Organic Chemistry, Vol. 78, Issue 16 https://doi.org/10.1021/jo401193e	journal	July 2013
The use of enzymes in organic synthesis and the life sciences: perspectives from the Swiss Industrial Biocatalysis Consortium (SIBC) Meyer, Hans-Peter; Eichhorn, Eric; Hanlon, Steven Catal. Sci. Technol., Vol. 3, Issue 1 https://doi.org/10.1039/C2CY20350B	journal	January 2013
Laccase-catalyzed synthesis of catechol thioethers by reaction of catechols with thiols using air as an oxidant Abdel-Mohsen, Heba T.; Conrad, Jürgen; Beifuss, Uwe Green Chem., Vol. 16, Issue 1 https://doi.org/10.1039/C3GC41968A	journal	January 2014
Radical-cations as reference chromogens in kinetic studies of ono-electron transfer reactions: pulse radiolysis studies of 2,2′-azinobis-(3-ethylbenzthiazoline-6-sulphonate) Wolfenden, Brian S.; Willson, Robin. L. J. Chem. Soc., Perkin Trans. 2, Issue 7 https://doi.org/10.1039/P29820000805	journal	January 1982
The E Factor: fifteen years on Sheldon, Roger A. Green Chemistry, Vol. 9, Issue 12 https://doi.org/10.1039/b713736m	journal	January 2007
A one-pot synthesis of 1,4-naphthoquinone-2,3-bis-sulfides catalysed by a commercial laccase Wellington, Kevin W.; Bokako, Refiloe; Raseroka, Nelly Green Chemistry, Vol. 14, Issue 9 https://doi.org/10.1039/c2gc35926j	journal	January 2012
A convenient guide to help select replacement solvents for dichloromethane in chromatography Taygerly, Joshua P.; Miller, Larry M.; Yee, Alicia Green Chemistry, Vol. 14, Issue 11 https://doi.org/10.1039/c2gc36064k	journal	January 2012
Synthesis of disulfides by laccase-catalyzed oxidative coupling of heterocyclic thiols Abdel-Mohsen, Heba T.; Sudheendran, Kavitha; Conrad, Jürgen Green Chemistry, Vol. 15, Issue 6 https://doi.org/10.1039/c3gc40106e	journal	January 2013
Fungal laccases – occurrence and properties Baldrian, Petr FEMS Microbiology Reviews, Vol. 30, Issue 2 https://doi.org/10.1111/j.1574-4976.2005.00010.x	journal	March 2006
The atom economy--a search for synthetic efficiency Trost, B. Science, Vol. 254, Issue 5037 https://doi.org/10.1126/science.1962206	journal	December 1991
Recent advances in 1,4-benzoquinone chemistry Abraham, Ignatious; Joshi, Rahul; Pardasani, Pushpa Journal of the Brazilian Chemical Society, Vol. 22, Issue 3 https://doi.org/10.1590/S0103-50532011000300002	journal	January 2011
Characterization of polyphenol oxidase from Chaetomium thermophile, a thermophilic fungus. Ishigami, Tadashi; Hirose, Yoshiteru; Yamada, Yuzo The Journal of General and Applied Microbiology, Vol. 34, Issue 5 https://doi.org/10.2323/jgam.34.401	journal	January 1988

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Laccase catalysis for the synthesis of bioactive compounds Kudanga, Tukayi; Nemadziva, Blessing; Le Roes-Hill, Marilize Applied Microbiology and Biotechnology, Vol. 101, Issue 1 https://doi.org/10.1007/s00253-016-7987-5	journal	November 2016
Laccase-catalyzed green synthesis and cytotoxic activity of novel pyrimidobenzothiazoles and catechol thioethers Abdel-Mohsen, H. T.; Conrad, J.; Harms, K. RSC Advances, Vol. 7, Issue 28 https://doi.org/10.1039/c6ra28102h	journal	January 2017
Efficient and sustainable laccase-catalyzed iodination of p -substituted phenols using KI as iodine source and aerial O ₂ as oxidant Sdahl, Mark; Conrad, Jürgen; Braunberger, Christina RSC Advances, Vol. 9, Issue 34 https://doi.org/10.1039/c9ra02541c	journal	January 2019
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