Carbon-oxygen bond formation by fungal laccases: cross-coupling of 2,5-dihydroxy-N-(2-hydroxyethyl)-benzamide with the solvents water, methanol, and other alcohols.

Carbon-oxygen bond formation by fungal laccases: cross-coupling of 2,5-dihydroxy-N-(2-hydroxyethyl)-benzamide with the solvents water, methanol, and other alcohols. Research Abstract Details 

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Carbon-oxygen bond formation by fungal laccases: cross-coupling of 2,5-dihydroxy-N-(2-hydroxyethyl)-benzamide with the solvents water, methanol, and other alcohols. Abstract Text:

Katrin Manda,Dirk ,Annett Mikolasch,Elke Hammer,Enrico Schmidt,Kerstin Thurow,Frieder Schauer,Katrin Manda,Dirk ,Annett Mikolasch,Elke Hammer,Enrico Schmidt,Kerstin Thurow,Frieder Schauer,

Laccase-catalyzed reactions lead to oxidation of the substrate via a cation radical, which has been described to undergo proton addition to form a quinonoid derivative or nucleophilic attack by itself producing homomolecular dimers. In this study, for the substrate 2,5-dihydroxy-N-(2-hydroxyethyl)-benzamide, we show that, besides the quinonoid form of substrate, all products formed are nonhomomolecular ones. Indeed, without addition of a reaction partner, heteromolecular products are formed from the quinonoid form of the laccase-substrate and the solvents water or methanol present in the incubation assay. Consequently, in laccase catalyzed syntheses performed in aqueous solutions or in the presence of methanol or other alcohols, undesirable heteromolecular coupling reactions between the laccase substrate and solvents must be taken into account. Additionally, it could be shown at the example of methanol and other alcohols that C-O-bound cross-coupling of dihydroxylated aromatic substances with the hydroxyl group of aliphatic alcohols can be catalyzed by fungal laccases.

Carbon-oxygen bond formation by fungal laccases: cross-coupling of 2,5-dihydroxy-N-(2-hydroxyethyl)-benzamide with the solvents water, methanol, and other alcohols. Publishing Authors By Initials

K Manda,D ,A Mikolasch,E Hammer,E Schmidt,K Thurow,F Schauer,K Manda,D ,A Mikolasch,E Hammer,E Schmidt,K Thurow,F Schauer,

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Carbon-oxygen bond formation by fungal laccases: cross-coupling of 2,5-dihydroxy-N-(2-hydroxyethyl)-benzamide with the solvents water, methanol, and other alcohols. Journal Published:

PUBLICATION TYPE: Research Support, Non-U.S. Gov

Journal: Applied microbiology and biotechnology

VOLUME: 76

Page Numbers: 407-16

Journal Abbreviation: Appl. Microbiol. Biotechnol.

ISSN: 0175-7598

DAY: 19

MONTH: 06

YEAR: 2007

Carbon-oxygen bond formation by fungal laccases: cross-coupling of 2,5-dihydroxy-N-(2-hydroxyethyl)-benzamide with the solvents water, methanol, and other alcohols. Information

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LANGUAGE: eng

NlmUniqueID: 8406612

Carbon-oxygen bond formation by fungal laccases: cross-coupling of 2,5-dihydroxy-N-(2-hydroxyethyl)-benzamide with the solvents water, methanol, and other alcohols. Keywords Mesh Terms:

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Grant and Affiliation Information for Carbon-oxygen bond formation by fungal laccases: cross-coupling of 2,5-dihydroxy-N-(2-hydroxyethyl)-benzamide with the solvents water, methanol, and other alcohols.

AFFILIATION: Institute for Microbiology, Ernst-Moritz-Arndt-University Greifswald, Friedrich-Ludwig-Jahn-Str. 15, 17487 Greifswald, Germany. manda@uni-greifswald.de

Country: Germany

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MEDLINETA: Appl Microbiol Biotechnol

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