Combined action of enzymes: the first domino reaction catalyzed by Agaricus bisporus

Leutbecher, Heiko; Hajdok, Szilvia; Braunberger, Christina; Neumann, Melanie; Mika, Sabine; Conrad, Jürgen; Beifuß, Uwe

doi:10.1039/b822977e

Cited by 58 publications

(21 citation statements)

References 41 publications

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“…In contrast to the homomolecular reactions described by Nicotra et al [38], Kordon et al [39] and in our study, the formation of heteroaromatic five-membered rings resulting from heteromolecular reactions of ortho-hydroquinones have been repeatedly studied [17][18][19][20][21][22].…”

Section: Second Reaction Typecontrasting

confidence: 65%

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Laccase-mediated multi-step homo- and heteromolecular reactions of ortho -dihydroxylated aromatic compounds and mono- or diaminated substances resulting in C C, C O and C N bonds

Hahn

Mikolasch

Kuhlisch

et al. 2015

Journal of Molecular Catalysis B: Enzymatic

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Section: Second Reaction Typecontrasting

confidence: 65%

“…Different types of heterocycles may be formed during laccase-catalyzed reactions. In this way five-membered rings such as benzofurans [15,16], dibenzofurans [17][18][19][20][21], thiazoles [22] as well as six-membered rings such as phenoxazinone chromophores [23][24][25] have been synthesized.…”

Section: Introductionmentioning

confidence: 99%

Laccase-mediated multi-step homo- and heteromolecular reactions of ortho -dihydroxylated aromatic compounds and mono- or diaminated substances resulting in C C, C O and C N bonds

Hahn

Mikolasch

Kuhlisch

et al. 2015

Journal of Molecular Catalysis B: Enzymatic

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“…Catechols can be replaced by phenol as substrate when the reactions are performed in the presence of a combination of catalytic amounts of a tyrosinase and a laccase. This is the first example of the combined action of a tyrosinase and a laccase for a domino process (Scheme ) 219…”

Section: Oxidation Of Activated Sp3 Ch Bonds With O2mentioning

confidence: 99%

Selective Catalytic Oxidation of CH Bonds with Molecular Oxygen

et al. 2012

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Although catalytic reductions, cross‐couplings, metathesis, and oxidation of CC double bonds are well established, the corresponding catalytic hydroxylations of CH bonds in alkanes, arenes, or benzylic (allylic) positions, particularly with O2, the cheapest, “greenest”, and most abundant oxidant, are severely lacking. Certainly, some promising examples in homogenous and heterogenous catalysis exist, as well as enzymes that can perform catalytic aerobic oxidations on various substrates, but these have never achieved an industrial‐scale, owing to a low space‐time‐yield and poor stability. This review illustrates recent advances in aerobic oxidation catalysis by discussing selected examples, and aims to stimulate further exciting work in this area. Theoretical work on catalyst precursors, resting states, and elementary steps, as well as model reactions complemented by spectroscopic studies provide detailed insight into the molecular mechanisms of oxidation catalyses and pave the way for preparative applications. However, O2 also poses a safety hazard, especially when used for large scale reactions, therefore sophisticated methodologies have been developed to minimize these risks and to allow convenient transfer onto industrial scale.

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“…Compounds 13 and 19 have also been synthesised by employing tyrosinase and laccase from A. bisporus and were obtained in 39 and 44% yields, respectively 25. Our method was higher yielding since compound 13 was obtained in 59% yield and compound 19 in 76% yield (Entries 8 and 19, respectively, Table 1; Fig.…”

Section: Resultsmentioning

confidence: 85%

One‐Pot Laccase‐Catalysed Synthesis of 5,6‐Dihydroxylated Benzo[b]furans and Catechol Derivatives, and Their Anticancer Activity

Wellington

Qwebani‐Ogunleye

Kolesnikova

et al. 2013

Archiv der Pharmazie

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A commercial laccase, Suberase® from Novozymes, was used to catalyse the synthesis of 5,6-dihydroxylated benzo[b]furans and catechol derivatives. The yields were, in some cases, similar to or better than that obtained by other enzymatic, chemical or electrochemical syntheses. The synthesised derivatives were screened against renal (TK10), melanoma (UACC62), breast (MCF7) and cervical (HeLa) cancer cell lines. GI50, TGI and LC50 are reported for the first time. Anticancer screening showed that the cytostatic effects of the 5,6-dihydroxylated benzo[b]furans were most effective against the melanoma (UACC62) cancer cell line with several compounds exhibiting potent growth inhibitory activities (GI50=0.77-9.76 µM), of which two compounds had better activity than the anticancer agent etoposide (GI50 0.89 µM). One compound exhibited potent activity (GI50=9.73 µM) against the renal (TK10) cancer cell line and two exhibited potent activity (GI50=8.79 and 9.30 µM) against the breast (MCF7) cancer cell line. These results encourage further studies of the 5,6-dihydroxylated benzo[b]furans for their potential application in anticancer therapy.

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Combined action of enzymes: the first domino reaction catalyzed by Agaricus bisporus

Cited by 58 publications

References 41 publications

Laccase-mediated multi-step homo- and heteromolecular reactions of ortho -dihydroxylated aromatic compounds and mono- or diaminated substances resulting in C C, C O and C N bonds

Laccase-mediated multi-step homo- and heteromolecular reactions of ortho -dihydroxylated aromatic compounds and mono- or diaminated substances resulting in C C, C O and C N bonds

Selective Catalytic Oxidation of CH Bonds with Molecular Oxygen

One‐Pot Laccase‐Catalysed Synthesis of 5,6‐Dihydroxylated Benzo[b]furans and Catechol Derivatives, and Their Anticancer Activity

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