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 00:00:00 EDT 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 Lab. (ORNL), Oak Ridge, TN (United States)

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

Grant/Contract Number:: AC05-00OR22725

OSTI ID:: 1376559

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

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 21 works

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