Ecofriendly syntheses of phenothiazones and related structures facilitated by laccase – A comparative study

Cannatelli, Mark D.; Ragauskas, Arthur J.

doi:10.1016/j.tetlet.2016.07.016

Ecofriendly syntheses of phenothiazones and related structures facilitated by laccase – A comparative study

Journal Article · Wed Jul 06 00:00:00 EDT 2016 · Tetrahedron Letters

DOI:https://doi.org/10.1016/j.tetlet.2016.07.016· OSTI ID:1327722

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

Georgia Inst. of Technology, Atlanta, GA (United States)
Georgia Inst. of Technology, Atlanta, GA (United States); Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States); Univ. of Tennessee, Knoxville, TN (United States)

The biocatalytic synthesis of phenothiazones and related compounds has been achieved in an aqueous system under mild conditions facilitated by laccase oxidation. It was found that by coupling 2-aminothiophenol directly with 1,4-quinones, the product yields could be significantly increased compared to generating the 1,4-quinones in situ from the corresponding hydroquinones via laccase oxidation. However, laccase still proved to be pivotal for achieving highest product yields by catalyzing the final oxidation step. Furthermore, a difference in reactivity of aromatic and aliphatic amines toward 1,4-naphthoquinone is observed. Furthermore, this study provides a sustainable approach to the synthesis of a biologically important class of compounds.

View Accepted Manuscript (DOE)

Research Organization:: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States). Joint Institute for Biological Sciences (JIBS)

Sponsoring Organization:: USDOE Office of Science (SC)

Grant/Contract Number:: AC05-00OR22725

OSTI ID:: 1327722

Journal Information:: Tetrahedron Letters, Journal Name: Tetrahedron Letters Journal Issue: 33 Vol. 57; ISSN 0040-4039

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

References (51)

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
One-Pot Laccase-Catalysed Synthesis of 5,6-Dihydroxylated Benzo[ b ]furans and Catechol Derivatives, and Their Anticancer Activity Wellington, Kevin W.; Qwebani-Ogunleye, Tozama; Kolesnikova, Natasha I. Archiv der Pharmazie, Vol. 346, Issue 4 https://doi.org/10.1002/ardp.201200413	journal	February 2013
Concerted Electron/Proton Transfer Mechanism in the Oxidation of Phenols by Laccase Galli, Carlo; Madzak, Catherine; Vadalà, Raffaella ChemBioChem, Vol. 14, Issue 18 https://doi.org/10.1002/cbic.201300531	journal	October 2013
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
Studien in der Methylenblaugruppe Bernthsen, August Justus Liebig's Annalen der Chemie, Vol. 230, Issue 2 https://doi.org/10.1002/jlac.18852300202	journal	January 1885
Ueber die Constitution der Oxzin und Thiazinfarbstoffe und ihre Beziehungen zu den Azoniumkörpern Kehrmann, F. Justus Liebig's Annalen der Chemie, Vol. 322, Issue 1 https://doi.org/10.1002/jlac.19023220102	journal	January 1902
Über Phenthiazone I. Chlor-phenthiazone und deren Leukoverbindungen Bodea, Cornel; Raileanu, Metodiu Justus Liebigs Annalen der Chemie, Vol. 614, Issue 1 https://doi.org/10.1002/jlac.19586140120	journal	July 1958
Über Phenothiazone, XVII1). Darstellung von Monomethyl-3H-phenothiazinonen-(3) Terdic, Marius Justus Liebigs Annalen der Chemie, Vol. 746, Issue 1 https://doi.org/10.1002/jlac.19717460120	journal	April 1971
Laccases: a never-ending story Giardina, Paola; Faraco, Vincenza; Pezzella, Cinzia Cellular and Molecular Life Sciences, Vol. 67, Issue 3 https://doi.org/10.1007/s00018-009-0169-1	journal	October 2009
How to enjoy laccases Pezzella, Cinzia; Guarino, Lucia; Piscitelli, Alessandra Cellular and Molecular Life Sciences, Vol. 72, Issue 5 https://doi.org/10.1007/s00018-014-1823-9	journal	January 2015
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
Bacterial laccases Sharma, P.; Goel, R.; Capalash, N. World Journal of Microbiology and Biotechnology, Vol. 23, Issue 6 https://doi.org/10.1007/s11274-006-9305-3	journal	November 2006
Laccase: new functions for an old enzyme Mayer, A. Phytochemistry, Vol. 60, Issue 6 https://doi.org/10.1016/S0031-9422(02)00171-1	journal	July 2002
Oxidative conjugation of catechols with proteins in insect skeletal systems Kramer, Karl J.; Kanost, Michael R.; Hopkins, Theodore L. Tetrahedron, Vol. 57, Issue 2 https://doi.org/10.1016/S0040-4020(00)00949-2	journal	January 2001
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
Synthesis of 3-(3,4-dihydroxyphenyl)-propionic acid derivatives by N-coupling of amines using laccase Mikolasch, Annett; Hammer, Elke; Jonas, Ulrike Tetrahedron, Vol. 58, Issue 38 https://doi.org/10.1016/S0040-4020(02)00872-4	journal	September 2002
The Effect of Ferrivine and Intramine on Syphilis. Harrison, L. W.; Mills, C. H. The Lancet, Vol. 187, Issue 4842 https://doi.org/10.1016/S0140-6736(01)14502-2	journal	June 1916
Evaluating laccase-facilitated coupling of phenolic acids to high-yield kraft pulps Chandra, Richard P.; Ragauskas, Arthur J. Enzyme and Microbial Technology, Vol. 30, Issue 7 https://doi.org/10.1016/S0141-0229(02)00020-0	journal	June 2002
Naphtho[2,3-b][1,4]-thiazine-5,10-diones and 3-substituted-1,4-dioxo-1,4-dihydronaphthalen-2-yl-thioalkanoate derivatives: Synthesis and biological evaluation as potential antibacterial and antifungal agents Tandon, Vishnu K.; Maurya, Hardesh K.; Yadav, Dharmendra B. Bioorganic & Medicinal Chemistry Letters, Vol. 16, Issue 22 https://doi.org/10.1016/j.bmcl.2006.08.060	journal	November 2006
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
2,3-Disubstituted-1,4-naphthoquinones, 12H-benzo[b]phenothiazine-6,11-diones and related compounds: Synthesis and Biological evaluation as potential antiproliferative and antifungal agents Tandon, Vishnu K.; Maurya, Hardesh K.; Tripathi, Ashutosh European Journal of Medicinal Chemistry, Vol. 44, Issue 3 https://doi.org/10.1016/j.ejmech.2008.06.025	journal	March 2009
Modification of high-lignin softwood kraft pulp with laccase and amino acids Witayakran, Suteera; Ragauskas, Arthur J. Enzyme and Microbial Technology, Vol. 44, Issue 3 https://doi.org/10.1016/j.enzmictec.2008.10.011	journal	March 2009
Potential applications of laccase-mediated coupling and grafting reactions: A review Kudanga, Tukayi; Nyanhongo, Gibson S.; Guebitz, Georg M. Enzyme and Microbial Technology, Vol. 48, Issue 3 https://doi.org/10.1016/j.enzmictec.2010.11.007	journal	March 2011
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
Laccase-assisted surface functionalization of lignocellulosics Kalia, Susheel; Thakur, Kamini; Kumar, Amit Journal of Molecular Catalysis B: Enzymatic, Vol. 102 https://doi.org/10.1016/j.molcatb.2014.01.014	journal	April 2014
Laccase-catalyzed synthesis of 2,3-ethylenedithio-1,4-quinones Cannatelli, Mark D.; Ragauskas, Arthur J. Journal of Molecular Catalysis B: Enzymatic, Vol. 119 https://doi.org/10.1016/j.molcatb.2015.05.016	journal	September 2015
Enzymatic thiol Michael addition using laccases: Multiple CS bond formation between p-hydroquinones and aromatic thiols Schlippert, Max; Mikolasch, Annett; Hahn, Veronika Journal of Molecular Catalysis B: Enzymatic, Vol. 126 https://doi.org/10.1016/j.molcatb.2015.12.012	journal	April 2016
Laccase-based biosensors for detection of phenolic compounds Rodríguez-Delgado, Melissa M.; Alemán-Nava, Gibrán S.; Rodríguez-Delgado, José Manuel TrAC Trends in Analytical Chemistry, Vol. 74 https://doi.org/10.1016/j.trac.2015.05.008	journal	December 2015
Shall We Dance? How A Multicopper Oxidase Chooses Its Electron Transfer Partner Quintanar, Liliana; Stoj, Christopher; Taylor, Alexander B. Accounts of Chemical Research, Vol. 40, Issue 6 https://doi.org/10.1021/ar600051a	journal	June 2007
Oxidation of Phenols, Anilines, and Benzenethiols by Fungal Laccases: Correlation between Activity and Redox Potentials as Well as Halide Inhibition ^† Xu, Feng Biochemistry, Vol. 35, Issue 23 https://doi.org/10.1021/bi952971a	journal	January 1996
Redox Reactions Catalyzed by Isolated Enzymes Monti, Daniela; Ottolina, Gianluca; Carrea, Giacomo Chemical Reviews, Vol. 111, Issue 7 https://doi.org/10.1021/cr100334x	journal	July 2011
Nuclear Amination Catalyzed by Fungal Laccases: Reaction Products of p -Hydroquinones and Primary Aromatic Amines Niedermeyer, Timo H. J.; Mikolasch, Annett; Lalk, Michael The Journal of Organic Chemistry, Vol. 70, Issue 6 https://doi.org/10.1021/jo048454s	journal	March 2005
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
A Study of Cysteamine Ionization in Solution by Raman Spectroscopy and Theoretical Modeling Riauba, Laurynas; Niaura, Gediminas; Eicher-Lorka, Olegas The Journal of Physical Chemistry A, Vol. 110, Issue 50 https://doi.org/10.1021/jp063816g	journal	November 2006
Use of Enzymes in the Manufacture of Active Pharmaceutical Ingredients—A Science and Safety-Based Approach To Ensure Patient Safety and Drug Quality Wells, Andrew S.; Finch, Gregory L.; Michels, Peter C. Organic Process Research & Development, Vol. 16, Issue 12 https://doi.org/10.1021/op300153b	journal	September 2012
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—a natural source for the synthesis of benzofuro[2,3-c]pyrazolin-5-ones Kidwai, Mazaahir; Jain, Arti; Sharma, Abha Catal. Sci. Technol., Vol. 3, Issue 1 https://doi.org/10.1039/C2CY20452E	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
LXIII.—Chemistry of lacquer (Urushi). Part I. Communication from the Chemical Society of Tokio Yoshida, Hikorokuro J. Chem. Soc., Trans., Vol. 43, Issue 0 https://doi.org/10.1039/CT8834300472	journal	January 1883
The E Factor: fifteen years on Sheldon, Roger A. Green Chemistry, Vol. 9, Issue 12 https://doi.org/10.1039/b713736m	journal	January 2007
O2 Reduction to H2O by the multicopper oxidases Solomon, Edward I.; Augustine, Anthony J.; Yoon, Jungjoo Dalton Transactions, Issue 30 https://doi.org/10.1039/b800799c	journal	January 2008
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
The structure and function of fungal laccases Thurston, C. F. Microbiology, Vol. 140, Issue 1 https://doi.org/10.1099/13500872-140-1-19	journal	January 1994
The Effect of some Oxidation Products of Phenothiazine on Liver Fluke (Fasciola Hepatica) in Vitro Mackie, Alexander; Raeburn, John British Journal of Pharmacology and Chemotherapy, Vol. 7, Issue 2 https://doi.org/10.1111/j.1476-5381.1952.tb01315.x	journal	June 1952
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
Biobleaching chemistry of laccase-mediator systems on high-lignin-content kraft pulps Chakar, Fadi S.; Ragauskas, Arthur J. Canadian Journal of Chemistry, Vol. 82, Issue 2 https://doi.org/10.1139/v03-195	journal	February 2004
Spatial structures of ascorbate oxidase, laccase and related proteins: implications for the catalytic mechanism Messerschmidt, Albrecht Multi-Copper Oxidases https://doi.org/10.1142/9789812830081_0002	book	June 1997
Novel β-Lactam Antibiotics Synthesized by Amination of Catechols Using Fungal Laccase Mikolasch, Annett; Wurster, Martina; Lalk, Michael CHEMICAL & PHARMACEUTICAL BULLETIN, Vol. 56, Issue 7 https://doi.org/10.1248/cpb.56.902	journal	January 2008
Investigations into Laccase-Mediator Delignification of Kraft Pulps Sealey, J.; Ragauskas, A. J.; Elder, T. J. Holzforschung, Vol. 53, Issue 5 https://doi.org/10.1515/HF.1999.082	journal	September 1999

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