Oxidative degradation of 3,4-dimethoxybenzyl alcohol and its methyl ether by the lignin peroxidase of Phanerochaete chrysosporium

Schmidt, H.; Haemmerli, S.; Schoemaker, Hans E.; Leisola, Matti

doi:10.1021/bi00430a053

Cited by 89 publications

(68 citation statements)

References 33 publications

(47 reference statements)

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“…Therefore, rotting wood contains more quinones than living wood. The following rotting wood quinones have been detected: (2), (11), (12), (13), (14), (15), the corresponding hydroquinones, and two bicyclic quinones (BOLLAG et al 1982;KIRK et al 1986;SCHMIDT et al 1989;SCHOEMAKER et al 1989;WARIISHI et al 1989WARIISHI et al , 1991ERIKSSON et al 1990: 309ff;TuoR et al 1992). One of these quinones, 1,4-benzoquinone (2), was attractive to C. tuberculifrons in our experiments.…”

Section: Quinones As Wood Components and Products Of Rotting Woodsupporting

confidence: 52%

The rhinoceros beetleCyphonistes tuberculifronsQuedenfeldt 1884 attracted by quinones (Coleoptera Scarabaeidae Dynastinae): primary olfactory attraction of a saprophagous beetle by its source of food?

1999

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Section: Quinones As Wood Components and Products Of Rotting Woodsupporting

confidence: 52%

The rhinoceros beetleCyphonistes tuberculifronsQuedenfeldt 1884 attracted by quinones (Coleoptera Scarabaeidae Dynastinae): primary olfactory attraction of a saprophagous beetle by its source of food?

1999

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“…[32]. No products were observed in experiments carried out in the absence of either the catalyst or the oxidant.…”

Section: Methodsmentioning

confidence: 94%

Iron porphyrins-catalysed oxidation of α-alkyl substituted mono and dimethoxylated benzyl alcohols

2008

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Abstract:The mechanisms of oxidation of a series of a-alkyl substituted mono and dimethoxylated benzyl alcohols catalysed by mesotetrakis(4-N-methylpyridynium)porphyrin iron (III) chloride (FeTMPyPCl) and meso-tetrakis(4-sulfonatophenyl)porphyrin iron (III) chloride (FeTSPPCl) in aqueous solution with KHSO 5 as oxygen atom donor and by meso-tetrakis(pentafluorophenyl)-porphyrin iron (III) chloride (FeTPFPPCl) in dichloromethane employing iodosylbenzene as oxidant have been investigated. In the highly polar aqueous medium an electron transfer mechanism is operating. With FeTMPyPCl, which is a much more efficient catalyst than FeTSPPCl due to the presence of stronger electron withdrawing substituents, formation of side-chain oxidation products accompanies generation of nuclear oxidation products. In the low polar solvent dichloromethane, two competing mechanism have been suggested: hydrogen atom transfer and formation of a complex between the active species iron-oxo porphyrin radical cation and the substrate.© Versita Warsaw and Springer-Verlag Berlin Heidelberg.

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“…Reversed phase HPLC was performed using a C 18 column, eluted isocratically with either 50% acetonitrile or 40% methanol or with a gradient (Schmidt et al 1989) with a flow rate of 1.0 ml min" 1 .…”

Section: Enzymatic Reactionsmentioning

confidence: 99%

“…Veratryl alcohol, a common assay Substrate for LiP (Tien and Kirk 1984), has a electropotential of 1.22 Vand is not oxidised by laccase (Fawer et al 1991). The LiP-catalysed reaction yields veratraldehyde 2 together with variable amounts of quinones 3 and 4 and ring opened products 5, resulting from attack of water and oxygen or active oxygen species on the initially formed radical cation of veratryl alcohol (Haemmerli et al 1987;Schmidt et al 1989).…”

Section: Abts S a Mediatormentioning

confidence: 99%

On the Mechanism of Oxidation of Non-Phenolic Lignin Model Compounds by the Laccase-ABTS Couple

Muheim

Fiechter

Harvey³

1992

Holzforschung

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SummaryOxidation of veratryl alcohol by laccase in the presence of ABTS (2,2'azino-bis(3-ethylbenzthiazoline-6-sulphonic acid) yields veratraldehyde, but differs to the reaction catalysed by lignin peroxidase (LiP) because ring-opened prodticts and quinones associated with the reactivity of radical cation intermediates are not formed. The laccase-ABTS couple is also unable to oxidise 1,4-dimethoxybenzene to benzoquinone. Similar results were obtained using horseradish peroxidase (HRP) and ABTS with H 2 O 2 s oxidant. These data favour the view that the mechanism of the ABTS-coupled reaction does not involve radical cation formation and that the reactivity of laccase-ABTS is not equivalent to that of LiP. Similarly, no evidence for radical cation formation could be obtained when syringaldehyde was substituted for ABTS. It is suggested that the reactivity observed toward non-phenolic lignin model compounds with these enzyme-coupled Systems involves a hydrogen atom abstraction mechanism. The importance of oxidation via hydrogen atom abstraction in lignin degradation remains to be elucidated.

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Oxidative degradation of 3,4-dimethoxybenzyl alcohol and its methyl ether by the lignin peroxidase of Phanerochaete chrysosporium

Cited by 89 publications

References 33 publications

The rhinoceros beetleCyphonistes tuberculifronsQuedenfeldt 1884 attracted by quinones (Coleoptera Scarabaeidae Dynastinae): primary olfactory attraction of a saprophagous beetle by its source of food?

The rhinoceros beetleCyphonistes tuberculifronsQuedenfeldt 1884 attracted by quinones (Coleoptera Scarabaeidae Dynastinae): primary olfactory attraction of a saprophagous beetle by its source of food?

Iron porphyrins-catalysed oxidation of α-alkyl substituted mono and dimethoxylated benzyl alcohols

On the Mechanism of Oxidation of Non-Phenolic Lignin Model Compounds by the Laccase-ABTS Couple

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