Production of a chiral alcohol, 1-(3,4-dihydroxyphenyl) ethanol, by mushroom tyrosinase
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2013
Authors
Brooks, Sarah J.Nikodinović-Runić, Jasmina
Martin, Leona
Doyle, Evelyn M.
O'Sullivan, Timothy
Guiry, Patrick J.
Coulombel, Lydie
Li, Zhi
O'Connor, Kevin
Article (Published version)
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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.
Keywords:
Tyrosinase / Oxidation / Chiral product / BiotransformationSource:
Biotechnology Letters, 2013, 35, 5, 779-783Publisher:
- Springer, Dordrecht
Funding / projects:
- Enterprise Ireland Research Scholarship Programme [BR/1999/043]
- Society for General Microbiology Presidents Award Scheme
- Irish Environmental Protection Agency Contributory Scholarship Programme [2001-CS-(17/26)]
DOI: 10.1007/s10529-013-1148-z
ISSN: 0141-5492
PubMed: 23355036
WoS: 000318510500017
Scopus: 2-s2.0-84876989904
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Institut za molekularnu genetiku i genetičko inženjerstvoTY - JOUR AU - Brooks, Sarah J. AU - Nikodinović-Runić, Jasmina AU - Martin, Leona AU - Doyle, Evelyn M. AU - O'Sullivan, Timothy AU - Guiry, Patrick J. AU - Coulombel, Lydie AU - Li, Zhi AU - O'Connor, Kevin PY - 2013 UR - https://imagine.imgge.bg.ac.rs/handle/123456789/624 AB - 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. PB - Springer, Dordrecht T2 - Biotechnology Letters T1 - Production of a chiral alcohol, 1-(3,4-dihydroxyphenyl) ethanol, by mushroom tyrosinase EP - 783 IS - 5 SP - 779 VL - 35 DO - 10.1007/s10529-013-1148-z ER -
@article{ author = "Brooks, Sarah J. and Nikodinović-Runić, Jasmina and Martin, Leona and Doyle, Evelyn M. and O'Sullivan, Timothy and Guiry, Patrick J. and Coulombel, Lydie and Li, Zhi and O'Connor, Kevin ", year = "2013", abstract = "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.", publisher = "Springer, Dordrecht", journal = "Biotechnology Letters", title = "Production of a chiral alcohol, 1-(3,4-dihydroxyphenyl) ethanol, by mushroom tyrosinase", pages = "783-779", number = "5", volume = "35", doi = "10.1007/s10529-013-1148-z" }
Brooks, S. J., Nikodinović-Runić, J., Martin, L., Doyle, E. M., O'Sullivan, T., Guiry, P. J., Coulombel, L., Li, Z.,& O'Connor, K.. (2013). Production of a chiral alcohol, 1-(3,4-dihydroxyphenyl) ethanol, by mushroom tyrosinase. in Biotechnology Letters Springer, Dordrecht., 35(5), 779-783. https://doi.org/10.1007/s10529-013-1148-z
Brooks SJ, Nikodinović-Runić J, Martin L, Doyle EM, O'Sullivan T, Guiry PJ, Coulombel L, Li Z, O'Connor K. Production of a chiral alcohol, 1-(3,4-dihydroxyphenyl) ethanol, by mushroom tyrosinase. in Biotechnology Letters. 2013;35(5):779-783. doi:10.1007/s10529-013-1148-z .
Brooks, Sarah J., Nikodinović-Runić, Jasmina, Martin, Leona, Doyle, Evelyn M., O'Sullivan, Timothy, Guiry, Patrick J., Coulombel, Lydie, Li, Zhi, O'Connor, Kevin , "Production of a chiral alcohol, 1-(3,4-dihydroxyphenyl) ethanol, by mushroom tyrosinase" in Biotechnology Letters, 35, no. 5 (2013):779-783, https://doi.org/10.1007/s10529-013-1148-z . .