Studies on the Laccase‐Catalyzed Oxidation of 4‐Hydroxy‐Chalcones

Grosso, Simone; Radaelli, Fabio; Fronza, Giovanni; Passarella, Daniele; Monti, Daniela; Riva, Sergio

doi:10.1002/adsc.201900190

Cited by 11 publications

(10 citation statements)

References 37 publications

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“…The C=O of compound 4 resonated at 190.17 ppm. This compared favorably with the literature data (Grosso et al 2019, Rosa et al 2019). The α-and βcarbon atoms of the carbonyl appeared at 122.89 and 145.41 ppm respectively.…”

Section: Resultssupporting

confidence: 86%

Synthesis and antimicrobial activities of some new sulfonyl phenoxides

2021

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Four new sulfonyl phenoxides were synthesized through O-sulfonylation reaction of phenolic compounds with 5-chloro-1-ethyl-2-methylimidazole-4-sulfonyl chloride in good yield. FT-IR, 1H-NMR, 13C-NMR, and DEPT 135 NMR were carried out to characterize and the thin layer chromatography (TLC) confirm the purity. Antimicrobial activities of the sulfonyl phenoxides against Gram-positive (methicillin-susceptible Staphylococcus aureus, methicillin-resistant Staphylococcus aureus, and Bacillus subtilis), Gram-negative (Pseudomonas aeruginosa, Escherichia coli, Klebsiella pneumoniae), and Candida albicans were carried out using the standard microbiological method. The antimicrobial activities were referenced to ciprofloxacin and itraconazole, antibacterial and antifungal drug respectively. The in vitro antimicrobial studies of 5-chloro-1-ethyl-2-methyl-1H-imidazole-4-sulfonyl(4-chloro-3-methyl)phenoxide and 5-chloro-1-ethyl-2-methyl-1H-imidazole-4-sulfonyl-2-methylphenoxide showed moderate activity against C. albicans. The four sulfonyl phenoxides had weak activities against Gram-positive and Gram-negative bacteria. Keywords: Sulfonyl phenoxides, Antimicrobial, Phenolic compounds, O-Sulfonylation reaction

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Section: Resultssupporting

confidence: 86%

Synthesis and antimicrobial activities of some new sulfonyl phenoxides

2021

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“…This improvement in the product properties has been explained by the multiplication of functional (hydroxyl) groups [ 53 ]. Recently, these types of products were prepared from several natural compounds such as piceid [ 54 ], lignols [ 55 ], rutin [ 56 ], caffeic acid [ 57 , 58 ], 4-hydroxychalcons [ 59 ], or isorhamnetin [ 59 ].…”

Section: Laccase-catalyzed Reactionsmentioning

confidence: 99%

Laccases and Tyrosinases in Organic Synthesis

Martı́nková

Křístková

Křen

2022

IJMS

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Laccases (Lac) and tyrosinases (TYR) are mild oxidants with a great potential in research and industry. In this work, we review recent advances in their use in organic synthesis. We summarize recent examples of Lac-catalyzed oxidation, homocoupling and heterocoupling, and TYR-catalyzed ortho-hydroxylation of phenols. We highlight the combination of Lac and TYR with other enzymes or chemical catalysts. We also point out the biological and pharmaceutical potential of the products, such as dimers of piceid, lignols, isorhamnetin, rutin, caffeic acid, 4-hydroxychalcones, thiols, hybrid antibiotics, benzimidazoles, benzothiazoles, pyrimidine derivatives, hydroxytyrosols, alkylcatechols, halocatechols, or dihydrocaffeoyl esters, etc. These products include radical scavengers; antibacterial, antiviral, and antitumor compounds; and building blocks for bioactive compounds and drugs. We summarize the available enzyme sources and discuss the scalability of their use in organic synthesis. In conclusion, we assume that the intensive use of laccases and tyrosinases in organic synthesis will yield new bioactive compounds and, in the long-term, reduce the environmental impact of industrial organic chemistry.

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“…More recently, this approach was successfully used to transform 4-hydroxy-chalcones of synthetic origin into the corresponding 2,3-DHB derivatives. Due to the presence of the conjugated system with the fully conjugated π-carbonyl group characterizing chalcones, a C-O dimer was obtained in mixture with the 2,3-DHB based products (Scheme 28) [117]. Nature has solved the lack of enantioselectivity in laccase-mediated synthesis of 2,3-DHBs by the action of the so-called "dirigent proteins" [118,119].…”

Section: • Homocouplingsmentioning

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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Studies on the Laccase‐Catalyzed Oxidation of 4‐Hydroxy‐Chalcones

Cited by 11 publications

References 37 publications

Synthesis and antimicrobial activities of some new sulfonyl phenoxides

Synthesis and antimicrobial activities of some new sulfonyl phenoxides

Laccases and Tyrosinases in Organic Synthesis

Biocatalysis with Laccases: An Updated Overview

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