Production of a chiral alcohol, 1-(3,4-dihydroxyphenyl) ethanol, by mushroom tyrosinase
| Autor: | Sarah J. Brooks, Jasmina Nikodinovic, Lydie Coulombel, Zhi Li, Kevin E. O’Connor, Leona B. Martin, Evelyn Doyle, Timothy P. O'Sullivan, Patrick J. Guiry |
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| Rok vydání: | 2013 |
| Předmět: |
Chiral product
Reducing agent Tyrosinase Bioengineering Alcohol Applied Microbiology and Biotechnology 03 medical and health sciences chemistry.chemical_compound Phenols Biotransformation Oxidation Organic chemistry Chromatography High Pressure Liquid Plant Proteins 030304 developmental biology 0303 health sciences Ethanol Monophenol Monooxygenase 030306 microbiology Chemistry Substrate (chemistry) Stereoisomerism General Medicine Phenylethyl Alcohol Ascorbic acid Mushroom tyrosinase Agaricales Oxidation-Reduction Biotechnology Nuclear chemistry |
| Zdroj: | Biotechnology Letters |
| Popis: | 1-(3,4-Dihydroxyphenyl) ethanol was produced biocatalytically for the first time using mushroom tyrosinase. 4-Ethylphenol at 1 mM was consumed over 12 min giving 0.23 mM 4-ethylcatechol and 0.36 mM (R/S)-1-(3,4-dihydroxyphenyl) ethanol (ee 0.5 %). Mushroom tyrosinase consumed 4-ethylphenol at 6.7 mu mol min(-1) mg protein(-1) while the rates of formation of 4-ethylcatechol and 1-(3,4-dihydroxyphenyl) ethanol were 1.1 and 1.9 mu mol min(-1) mg protein(-1). Addition of the ascorbic acid, as a reducing agent to biotransformation reactions, increased 4-ethylcatechol formation by 340 %. However, accumulation of 1-(3,4-dihydroxyphenyl) ethanol was not observed in the presence of ascorbic acid. While the 1-(3,4-dihydroxyphenyl) ethanol was racemic, it is the first chiral product produced by tyrosinase starting from a non-chiral substrate. |
| Databáze: | OpenAIRE |
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