Selective biotransformation reactions on (±)-aryl alkyl ketones, (±)-benzoxazines, and d-arabino- and d-threo-hydroxyalkyltriazoles
Abstract The capabilities of porcine pancreatic lipase (PPL), Candida antarctica lipase (CAL), and Candida rugosa lipase (CRL) were evaluated for enantio- and/or regioselective acetylation/deacetylation of (±)-2,4-diacetoxyphenyl alkyl ketones, (±)-4-alkyl-3,4-dihydro-3-hydroxyalkyl-2 H -1,3-benzoxa...
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Walter de Gruyter GmbH
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crdegruyter:10.1351/pac200173010167 2023-05-15T14:07:37+02:00 Selective biotransformation reactions on (±)-aryl alkyl ketones, (±)-benzoxazines, and d-arabino- and d-threo-hydroxyalkyltriazoles Raunak Prasad, Ashok K. Shakil, Najam A. Himanshu Parmar, Virinder S. 2001 http://dx.doi.org/10.1351/pac200173010167 https://www.degruyter.com/view/journals/pac/73/1/article-p167.xml https://www.degruyter.com/document/doi/10.1351/pac200173010167/xml https://www.degruyter.com/document/doi/10.1351/pac200173010167/pdf en eng Walter de Gruyter GmbH Pure and Applied Chemistry volume 73, issue 1, page 167-174 ISSN 1365-3075 0033-4545 General Chemical Engineering General Chemistry journal-article 2001 crdegruyter https://doi.org/10.1351/pac200173010167 2022-04-14T05:06:45Z Abstract The capabilities of porcine pancreatic lipase (PPL), Candida antarctica lipase (CAL), and Candida rugosa lipase (CRL) were evaluated for enantio- and/or regioselective acetylation/deacetylation of (±)-2,4-diacetoxyphenyl alkyl ketones, (±)-4-alkyl-3,4-dihydro-3-hydroxyalkyl-2 H -1,3-benzoxazines, and d- arabino and d- threo -polyhydroxyalkyltriazoles in organic solvents. PPL in tetrahydrofuran (THF) exhibited high to moderate enantioselectivity during the deacetylation of (±)-2,4-diacetoxyaryl alkyl ketones and acetylation of (±)-3-hydroxyalkyl-2 H -1,3-benzoxazines. Together with enantioselectivity, PPL in THF also showed exclusive regioselectivity for the deacetylation of para -acetoxy over the ortho -acetoxy function, with respect to the nuclear carbonyl group in 2,4-diacetoxyphenyl alkyl ketones. CAL in diisopropyl ether (DIPE) and PPL in THF exhibited exclusive selectivity for the acetylation of primary hydroxyl over secondary hydroxyl group(s) of d- arabino - and d- threo -polyhydroxyalkyltriazoles. Article in Journal/Newspaper Antarc* Antarctica De Gruyter (via Crossref) Rugosa ENVELOPE(-61.250,-61.250,-62.633,-62.633) Pure and Applied Chemistry 73 1 167 174 |
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De Gruyter (via Crossref) |
op_collection_id |
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English |
topic |
General Chemical Engineering General Chemistry |
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General Chemical Engineering General Chemistry Raunak Prasad, Ashok K. Shakil, Najam A. Himanshu Parmar, Virinder S. Selective biotransformation reactions on (±)-aryl alkyl ketones, (±)-benzoxazines, and d-arabino- and d-threo-hydroxyalkyltriazoles |
topic_facet |
General Chemical Engineering General Chemistry |
description |
Abstract The capabilities of porcine pancreatic lipase (PPL), Candida antarctica lipase (CAL), and Candida rugosa lipase (CRL) were evaluated for enantio- and/or regioselective acetylation/deacetylation of (±)-2,4-diacetoxyphenyl alkyl ketones, (±)-4-alkyl-3,4-dihydro-3-hydroxyalkyl-2 H -1,3-benzoxazines, and d- arabino and d- threo -polyhydroxyalkyltriazoles in organic solvents. PPL in tetrahydrofuran (THF) exhibited high to moderate enantioselectivity during the deacetylation of (±)-2,4-diacetoxyaryl alkyl ketones and acetylation of (±)-3-hydroxyalkyl-2 H -1,3-benzoxazines. Together with enantioselectivity, PPL in THF also showed exclusive regioselectivity for the deacetylation of para -acetoxy over the ortho -acetoxy function, with respect to the nuclear carbonyl group in 2,4-diacetoxyphenyl alkyl ketones. CAL in diisopropyl ether (DIPE) and PPL in THF exhibited exclusive selectivity for the acetylation of primary hydroxyl over secondary hydroxyl group(s) of d- arabino - and d- threo -polyhydroxyalkyltriazoles. |
format |
Article in Journal/Newspaper |
author |
Raunak Prasad, Ashok K. Shakil, Najam A. Himanshu Parmar, Virinder S. |
author_facet |
Raunak Prasad, Ashok K. Shakil, Najam A. Himanshu Parmar, Virinder S. |
author_sort |
Raunak |
title |
Selective biotransformation reactions on (±)-aryl alkyl ketones, (±)-benzoxazines, and d-arabino- and d-threo-hydroxyalkyltriazoles |
title_short |
Selective biotransformation reactions on (±)-aryl alkyl ketones, (±)-benzoxazines, and d-arabino- and d-threo-hydroxyalkyltriazoles |
title_full |
Selective biotransformation reactions on (±)-aryl alkyl ketones, (±)-benzoxazines, and d-arabino- and d-threo-hydroxyalkyltriazoles |
title_fullStr |
Selective biotransformation reactions on (±)-aryl alkyl ketones, (±)-benzoxazines, and d-arabino- and d-threo-hydroxyalkyltriazoles |
title_full_unstemmed |
Selective biotransformation reactions on (±)-aryl alkyl ketones, (±)-benzoxazines, and d-arabino- and d-threo-hydroxyalkyltriazoles |
title_sort |
selective biotransformation reactions on (±)-aryl alkyl ketones, (±)-benzoxazines, and d-arabino- and d-threo-hydroxyalkyltriazoles |
publisher |
Walter de Gruyter GmbH |
publishDate |
2001 |
url |
http://dx.doi.org/10.1351/pac200173010167 https://www.degruyter.com/view/journals/pac/73/1/article-p167.xml https://www.degruyter.com/document/doi/10.1351/pac200173010167/xml https://www.degruyter.com/document/doi/10.1351/pac200173010167/pdf |
long_lat |
ENVELOPE(-61.250,-61.250,-62.633,-62.633) |
geographic |
Rugosa |
geographic_facet |
Rugosa |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Pure and Applied Chemistry volume 73, issue 1, page 167-174 ISSN 1365-3075 0033-4545 |
op_doi |
https://doi.org/10.1351/pac200173010167 |
container_title |
Pure and Applied Chemistry |
container_volume |
73 |
container_issue |
1 |
container_start_page |
167 |
op_container_end_page |
174 |
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1766279627902287872 |