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

Cannatelli, Mark D.; Ragauskas, Arthur J.

doi:10.1016/j.molcatb.2015.05.016

Cited by 25 publications

(8 citation statements)

References 31 publications

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“…Phenothiazines are heterocyclic sulphur compounds applicable in many areas of medicine, in particular in the treatment of neurodegenerative diseases such as Alzheimer’s and Parkinson’s diseases [ 74 ]. Considering that laccases can oxidize hydroquinones and catechols to produce in situ p - and o -quinones, the cross-coupling reactions involving sulphur-based nucleophiles (1,2-ethanedithiol or 2-aminothiophenol) were exploited providing a sustainable approach for the synthesis of 2,3-ethylenedithio1,4-quinone and phenothiazine substructures ( Scheme 16 A) [ 97 , 109 ].…”

Section: Application Of Laccases In Bio-oxidative Synthesis Of Heterocyclic Compoundsmentioning

confidence: 99%

Laccases: Versatile Biocatalysts for the Synthesis of Heterocyclic Cores

2021

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Laccases are multicopper oxidases that have shown a great potential in various biotechnological and green chemistry processes mainly due to their high relative non-specific oxidation of phenols, arylamines and some inorganic metals, and their high redox potentials that can span from 500 to 800 mV vs. SHE. Other advantages of laccases include the use of readily available oxygen as a second substrate, the formation of water as a side-product and no requirement for cofactors. Importantly, addition of low-molecular-weight redox mediators that act as electron shuttles, promoting the oxidation of complex bulky substrates and/or of higher redox potential than the enzymes themselves, can further expand their substrate scope, in the so-called laccase-mediated systems (LMS). Laccase bioprocesses can be designed for efficiency at both acidic and basic conditions since it is known that fungal and bacterial laccases exhibit distinct optimal pH values for the similar phenolic and aromatic amines. This review covers studies on the synthesis of five- and six-membered ring heterocyclic cores, such as benzimidazoles, benzofurans, benzothiazoles, quinazoline and quinazolinone, phenazine, phenoxazine, phenoxazinone and phenothiazine derivatives. The enzymes used and the reaction protocols are briefly outlined, and the mechanistic pathways described.

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Section: Application Of Laccases In Bio-oxidative Synthesis Of Heterocyclic Compoundsmentioning

confidence: 99%

Laccases: Versatile Biocatalysts for the Synthesis of Heterocyclic Cores

2021

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“…160 U mg À1 of protein using ABTS as a chromogenic substrate. 20 2.2 Preparation of PANI/MWCNT composite PANI/MWCNT composite was obtained by in situ enzymatic aniline polymerization with atmospheric oxygen as terminal oxidant. The fungal laccase catalyzed aniline polymerization in the presence of aniline dimer as a redox enhancer of enzymatic polymerization.…”

Section: Methodsmentioning

confidence: 99%

Enhanced performance of a flexible supercapacitor due to a combination of the pseudocapacitances of both a PANI/MWCNT composite electrode and a gel polymer redox electrolyte

et al. 2017

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“…When conducting the mentioned processes in the presence of a bidentate nucleophile, cyclic structures can be obtained via a sequence of one inter-and one intra-molecular laccase-mediated 1,4-additions. As an example, in 2015, Cannatelli et al reported a biocatalyzed domino synthesis of 2,3-ethylenedithio-1,4-quinones based on the laccase-activation of the C2 and C3 positions in the presence of 1,2-ethanedithiol (Scheme 30) [124].…”

Section: • Heterocouplingsmentioning

confidence: 99%

Biocatalysis with Laccases: An Updated Overview

et al. 2020

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Laccases are multicopper oxidases, which have been widely investigated in recent decades thanks to their ability to oxidize organic substrates to the corresponding radicals while producing water at the expense of molecular oxygen. Besides their successful (bio)technological applications, for example, in textile, petrochemical, and detoxifications/bioremediations industrial processes, their synthetic potentialities for the mild and green preparation or selective modification of fine chemicals are of outstanding value in biocatalyzed organic synthesis. Accordingly, this review is focused on reporting and rationalizing some of the most recent and interesting synthetic exploitations of laccases. Applications of the so-called laccase-mediator system (LMS) for alcohol oxidation are discussed with a focus on carbohydrate chemistry and natural products modification as well as on bio- and chemo-integrated processes. The laccase-catalyzed Csp2-H bonds activation via monoelectronic oxidation is also discussed by reporting examples of enzymatic C-C and C-O radical homo- and hetero-couplings, as well as of aromatic nucleophilic substitutions of hydroquinones or quinoids. Finally, the laccase-initiated domino/cascade synthesis of valuable aromatic (hetero)cycles, elegant strategies widely documented in the literature across more than three decades, is also presented.

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

Cited by 25 publications

References 31 publications

Laccases: Versatile Biocatalysts for the Synthesis of Heterocyclic Cores

Laccases: Versatile Biocatalysts for the Synthesis of Heterocyclic Cores

Enhanced performance of a flexible supercapacitor due to a combination of the pseudocapacitances of both a PANI/MWCNT composite electrode and a gel polymer redox electrolyte

Biocatalysis with Laccases: An Updated Overview

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