On the reactivity of the Melanocarpus albomyces laccase and formation of coniferyl alcohol dehydropolymer (DHP) in the presence of ionic liquid 1-allyl-3-methylimidazolium chloride

Lahtinen, Maarit; Viikari, Liisa; Karhunen, Pirkko; Asikkala, Janne; Kruus, Kristiina; Kilpeläinen, Ilkka

doi:10.1016/j.molcatb.2012.09.005

Cited by 14 publications

(13 citation statements)

References 45 publications

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“…Earlier studies reported laccases from plants31 and fungi27, 29, 31 that are capable of dimerizing coniferyl alcohol 2 to pinoresinol 3 . In addition, horseradish peroxidase (HRP) has been described to catalyze this reaction 23.…”

Section: Resultsmentioning

confidence: 99%

“…Promising biocatalytic approaches have been reported that employ laccases or peroxidases as catalysts and coniferyl alcohol as starting material 23. 27–29 A general drawback of these reactions is that they suffer from low selectivity and, therefore, low product concentrations (isolated yields of 4 or 10 %) 23. 29 Moreover, the starting compound for this reaction, coniferyl alcohol, is quite expensive.…”

Section: Introductionmentioning

confidence: 99%

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Two‐Step One‐Pot Synthesis of Pinoresinol from Eugenol in an Enzymatic Cascade

et al. 2015

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The phytoestrogen pinoresinol is a high‐value compound that has a protective effect against diverse health disorders, and thus is of interest for the pharmaceutical industry. Isolation of pinoresinol from plants suffers from low yields, and its chemical synthesis involves several work‐up steps. In this study we devised a novel two‐step one‐pot enzymatic cascade combining a vanillyl‐alcohol oxidase and a laccase for the production of pinoresinol from eugenol via the intermediate coniferyl alcohol. Along with the well‐characterized vanillyl‐alcohol oxidase from Penicillium simplicissimum used to catalyze the oxidation of eugenol, enzyme screening revealed three bacterial laccases that were appropriate for the synthesis of pinoresinol from coniferyl alcohol. The cascade was optimized regarding enzyme ratios, pH value, and the presence of organic solvents. Under optimized conditions, pinoresinol concentration achieved 4.4 mM (1.6 g l−1), and this compound was isolated and analyzed.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Two‐Step One‐Pot Synthesis of Pinoresinol from Eugenol in an Enzymatic Cascade

et al. 2015

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“…To confirmt he presence of structural motifs that are also in natural lignin, 2D HSQC NMR analysis was performed (see Figure 5). From the obtained spectrum, clearly signalsb elonging to lignin a-O-4, [29] b-O-4, b-b, b-5 and 5-5' could be observed. Alsoadibenzodioxocin fragmentw as identifieda nd confirmed based on previous findings.…”

Section: Characterizationoft He Lignin-like Oligomers In the Water-insoluble Fractionmentioning

confidence: 94%

A Biocatalytic One‐Pot Approach for the Preparation of Lignin Oligomers Using an Oxidase/Peroxidase Cascade Enzyme System

et al. 2017

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Syntheticl ignin wasp reparedb iocatalytically in ao ne-pot, two-stepr eactionu sing an oxidase/peroxidasec ascade enzyme system. Using eugenoli nc ombination with eugenolo xidase and a peroxidase,l ignin-like material was produced. The cascade reactiont akes advantage of the ability of the oxidase to produce coniferyla lcohol and hydrogen peroxide from eugenola nd molecular oxygen. The hydrogenp eroxide is usedb yt he peroxidasef or the formation of crosslinks that typify lignin. As eugenol oxidase has ab road substrate acceptance profile, also 4-allylphenol (chavicol) and 4-allyl-2,6-dimethoxyphenol could be used as precursors of the synthetic lignin. As ar esult, all three naturally occurring monolignols couldb ep repared and incorporated in the synthetic lignin. Ther eaction was optimized in order to achievet he highest possible yield of insoluble lignin oligomers and scaled up to 1g ram.A nalysis of the water-insoluble product by gel permeation chromatography revealed the formation of relatively small lignin oligomers ( % 1000 dalton). By using twodimensional heteronuclear single quantum coherence nuclear magnetic resonance spectroscopy (2D HSQC NMR) analysis it could be demonstratedt hat the material contained a-O-4/b-O-4, b-O-4, b-b, b-5 linkages and dibenzodioxocin units.All these featuresindicate that the biocatalytically produced material closely resembles natural lignin. While 54% of eugenol wasc onverted into water-insoluble oligomers, the remaining substrate was converted into watersoluble dimersa nd tetramers which are important lignin model compounds.T herefore,t he presented method represents av aluable andf acile biocatalytic approachf or the preparation of lignin-like material and potentially valuable chemicals.

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“…The most deactivating ILs contain anions that are capable of breaking hydrogen bonds, such as [Cl]. Lahtinen et al found that prolonged incubation of Melanocarpus albomyces laccase in the presence of an IL caused an additional inactivating effect . However, without understanding how and with which enzyme structures the IL ions interact at the molecular level, it was not possible to explain these observations.…”

Section: Application Of Ils To Biomoleculesmentioning

confidence: 99%

Recent advances in exploiting ionic liquids for biomolecules: Solubility, stability and applications

Sivapragasam

Moniruzzaman

Goto

2016

Biotechnology Journal

171

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The technological utility of biomolecules (e.g. proteins, enzymes and DNA) can be significantly enhanced by combining them with ionic liquids (ILs) - potentially attractive "green" and "designer" solvents - rather than using in conventional organic solvents or water. In recent years, ILs have been used as solvents, cosolvents, and reagents for biocatalysis, biotransformation, protein preservation and stabilization, DNA solubilization and stabilization, and other biomolecule-based applications. Using ILs can dramatically enhance the structural and chemical stability of proteins, DNA, and enzymes. This article reviews the recent technological developments of ILs in protein-, enzyme-, and DNA-based applications. We discuss the different routes to increase biomolecule stability and activity in ILs, and the design of biomolecule-friendly ILs that can dissolve biomolecules with minimum alteration to their structure. This information will be helpful to design IL-based processes in biotechnology and the biological sciences that can serve as novel and selective processes for enzymatic reactions, protein and DNA stability, and other biomolecule-based applications.

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On the reactivity of the Melanocarpus albomyces laccase and formation of coniferyl alcohol dehydropolymer (DHP) in the presence of ionic liquid 1-allyl-3-methylimidazolium chloride

Cited by 14 publications

References 45 publications

Two‐Step One‐Pot Synthesis of Pinoresinol from Eugenol in an Enzymatic Cascade

Two‐Step One‐Pot Synthesis of Pinoresinol from Eugenol in an Enzymatic Cascade

A Biocatalytic One‐Pot Approach for the Preparation of Lignin Oligomers Using an Oxidase/Peroxidase Cascade Enzyme System

Recent advances in exploiting ionic liquids for biomolecules: Solubility, stability and applications

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