Enantioselective Hydroxylation of 4-Alkylphenols by Vanillyl Alcohol Oxidase
Vanillyl alcohol oxidase (VAO) from Penicillium simplicissimum catalyzes the enantioselective hydroxylation of 4-ethylphenol, 4-propylphenol, and 2-methoxy-4-propylphenol into 1-(4'-hydroxyphenyl)ethanol, 1-(4'-hydroxyphenyl)propanol, and 1-(4'-hydroxy-3'-methoxyphenyl)propanol,...
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1998
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Online Access: | https://hdl.handle.net/11370/6a44da4b-497f-4402-aab3-9f177a39f3bb https://research.rug.nl/en/publications/6a44da4b-497f-4402-aab3-9f177a39f3bb https://doi.org/10.1002/(SICI)1097-0290(19980720)59:2<171::AID-BIT5>3.0.CO;2-E https://pure.rug.nl/ws/files/14538285/1998BiotechnolBioengDrijfhout.pdf |
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ftunigroningenpu:oai:pure.rug.nl:publications/6a44da4b-497f-4402-aab3-9f177a39f3bb 2024-06-02T07:58:23+00:00 Enantioselective Hydroxylation of 4-Alkylphenols by Vanillyl Alcohol Oxidase Drijfhout, Falko P. Fraaije, Marco W. Jongejan, Hugo Berkel, Willem J.H. van Franssen, Maurice C.R. 1998 application/pdf https://hdl.handle.net/11370/6a44da4b-497f-4402-aab3-9f177a39f3bb https://research.rug.nl/en/publications/6a44da4b-497f-4402-aab3-9f177a39f3bb https://doi.org/10.1002/(SICI)1097-0290(19980720)59:2<171::AID-BIT5>3.0.CO;2-E https://pure.rug.nl/ws/files/14538285/1998BiotechnolBioengDrijfhout.pdf eng eng https://research.rug.nl/en/publications/6a44da4b-497f-4402-aab3-9f177a39f3bb info:eu-repo/semantics/openAccess Drijfhout , F P , Fraaije , M W , Jongejan , H , Berkel , W J H V & Franssen , M C R 1998 , ' Enantioselective Hydroxylation of 4-Alkylphenols by Vanillyl Alcohol Oxidase ' , Biotechnology and Bioengineering , vol. 59 , no. 2 . https://doi.org/10.1002/(SICI)1097-0290(19980720)59:2<171::AID-BIT5>3.0.CO;2-E 4-vinylphenol enantioselectivity covalent flavoprotein vanillyl alcohol oxidase 4-alkylphenols article 1998 ftunigroningenpu https://doi.org/10.1002/(SICI)1097-0290(19980720)59:2<171::AID-BIT5>3.0.CO;2-E 2024-05-07T19:24:48Z Vanillyl alcohol oxidase (VAO) from Penicillium simplicissimum catalyzes the enantioselective hydroxylation of 4-ethylphenol, 4-propylphenol, and 2-methoxy-4-propylphenol into 1-(4'-hydroxyphenyl)ethanol, 1-(4'-hydroxyphenyl)propanol, and 1-(4'-hydroxy-3'-methoxyphenyl)propanol, respectively, with an ee of 94% for the R enantiomer. The stereochemical outcome of the reactions was established by comparing the chiral GC retention times of the products to those of chiral alcohols obtained by the action of the lipases from Candida antarctica and Pseudomonas cepacia. Isotope labeling experiments revealed that the oxygen atom incorporated into the alcoholic products is derived from water. During the VAO-mediated conversion of 4-ethylphenol/4-propylphenol, 4-vinylphenol/4-propenylphenol are formed as side products. With 2-methoxy-4-propylphenol as a substrate, this competing side reaction is nearly abolished, resulting in less than 1% of the vinylic product, isoeugenol. The VAO-mediated conversion of 4-alkylphenols also results in small amounts of phenolic ketones indicative for a consecutive oxidation step. Article in Journal/Newspaper Antarc* Antarctica University of Groningen research database |
institution |
Open Polar |
collection |
University of Groningen research database |
op_collection_id |
ftunigroningenpu |
language |
English |
topic |
4-vinylphenol enantioselectivity covalent flavoprotein vanillyl alcohol oxidase 4-alkylphenols |
spellingShingle |
4-vinylphenol enantioselectivity covalent flavoprotein vanillyl alcohol oxidase 4-alkylphenols Drijfhout, Falko P. Fraaije, Marco W. Jongejan, Hugo Berkel, Willem J.H. van Franssen, Maurice C.R. Enantioselective Hydroxylation of 4-Alkylphenols by Vanillyl Alcohol Oxidase |
topic_facet |
4-vinylphenol enantioselectivity covalent flavoprotein vanillyl alcohol oxidase 4-alkylphenols |
description |
Vanillyl alcohol oxidase (VAO) from Penicillium simplicissimum catalyzes the enantioselective hydroxylation of 4-ethylphenol, 4-propylphenol, and 2-methoxy-4-propylphenol into 1-(4'-hydroxyphenyl)ethanol, 1-(4'-hydroxyphenyl)propanol, and 1-(4'-hydroxy-3'-methoxyphenyl)propanol, respectively, with an ee of 94% for the R enantiomer. The stereochemical outcome of the reactions was established by comparing the chiral GC retention times of the products to those of chiral alcohols obtained by the action of the lipases from Candida antarctica and Pseudomonas cepacia. Isotope labeling experiments revealed that the oxygen atom incorporated into the alcoholic products is derived from water. During the VAO-mediated conversion of 4-ethylphenol/4-propylphenol, 4-vinylphenol/4-propenylphenol are formed as side products. With 2-methoxy-4-propylphenol as a substrate, this competing side reaction is nearly abolished, resulting in less than 1% of the vinylic product, isoeugenol. The VAO-mediated conversion of 4-alkylphenols also results in small amounts of phenolic ketones indicative for a consecutive oxidation step. |
format |
Article in Journal/Newspaper |
author |
Drijfhout, Falko P. Fraaije, Marco W. Jongejan, Hugo Berkel, Willem J.H. van Franssen, Maurice C.R. |
author_facet |
Drijfhout, Falko P. Fraaije, Marco W. Jongejan, Hugo Berkel, Willem J.H. van Franssen, Maurice C.R. |
author_sort |
Drijfhout, Falko P. |
title |
Enantioselective Hydroxylation of 4-Alkylphenols by Vanillyl Alcohol Oxidase |
title_short |
Enantioselective Hydroxylation of 4-Alkylphenols by Vanillyl Alcohol Oxidase |
title_full |
Enantioselective Hydroxylation of 4-Alkylphenols by Vanillyl Alcohol Oxidase |
title_fullStr |
Enantioselective Hydroxylation of 4-Alkylphenols by Vanillyl Alcohol Oxidase |
title_full_unstemmed |
Enantioselective Hydroxylation of 4-Alkylphenols by Vanillyl Alcohol Oxidase |
title_sort |
enantioselective hydroxylation of 4-alkylphenols by vanillyl alcohol oxidase |
publishDate |
1998 |
url |
https://hdl.handle.net/11370/6a44da4b-497f-4402-aab3-9f177a39f3bb https://research.rug.nl/en/publications/6a44da4b-497f-4402-aab3-9f177a39f3bb https://doi.org/10.1002/(SICI)1097-0290(19980720)59:2<171::AID-BIT5>3.0.CO;2-E https://pure.rug.nl/ws/files/14538285/1998BiotechnolBioengDrijfhout.pdf |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Drijfhout , F P , Fraaije , M W , Jongejan , H , Berkel , W J H V & Franssen , M C R 1998 , ' Enantioselective Hydroxylation of 4-Alkylphenols by Vanillyl Alcohol Oxidase ' , Biotechnology and Bioengineering , vol. 59 , no. 2 . https://doi.org/10.1002/(SICI)1097-0290(19980720)59:2<171::AID-BIT5>3.0.CO;2-E |
op_relation |
https://research.rug.nl/en/publications/6a44da4b-497f-4402-aab3-9f177a39f3bb |
op_rights |
info:eu-repo/semantics/openAccess |
op_doi |
https://doi.org/10.1002/(SICI)1097-0290(19980720)59:2<171::AID-BIT5>3.0.CO;2-E |
_version_ |
1800741707154718720 |