Production of a chiral alcohol, 1-(3,4-dihydroxyphenyl) ethanol, by mushroom tyrosinase.
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 μmol 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 μmol 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.
School of Biomolecular and Biomedical Science, University College Dublin, Belfield, Dublin 4, Ireland. drsbrooks@gmail.com
Sarah J
SJ
Brooks
Jasmina
J
Nikodinovic
Leona
L
Martin
Evelyn M
EM
Doyle
Timothy
T
O'Sullivan
Patrick J
PJ
Guiry
Lydie
L
Coulombel
Zhi
Z
Li
Kevin E
KE
O'Connor
D000363:Agaricales / Q000201:enzymology*; D001711:Biotransformation; D002851:Chromatography, High Pressure Liquid; D014442:Monophenol Monooxygenase / Q000378:metabolism*; D010084:Oxidation-Reduction; D010636:Phenols / Q000032:analysis / Q000378:metabolism; D010626:Phenylethyl Alcohol / Q000031:analogs & derivatives* / Q000032:analysis / Q000378:metabolism; D010940:Plant Proteins / Q000378:metabolism*; D013237:Stereoisomerism
D010636:Phenols; D010940:Plant Proteins; C005975:3,4-dihydroxyphenylethanol; C042291:4-ethylphenol; D014442:Monophenol Monooxygenase; D010626:Phenylethyl Alcohol