Combining regio‐ and enantioselectivity of lipases for the preparation of ( R)‐4‐chloro‐2‐butanol
Abstract Preparation of 98% ee ( R )‐4‐chloro‐2‐butanol was carried out by the enzymatic hydrolysis of chlorohydrin esters, using fungal resting cells and commercial enzymes. Hydrolyzes were carried out using lipases from Candida antarctica (Novozym 435®), C. rugosa, Rhizomucor miehei (Lipozyme® IM)...
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Online Access: | http://dx.doi.org/10.1002/chir.20339 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fchir.20339 https://onlinelibrary.wiley.com/doi/pdf/10.1002/chir.20339 |
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crwiley:10.1002/chir.20339 2024-06-23T07:47:42+00:00 Combining regio‐ and enantioselectivity of lipases for the preparation of ( R)‐4‐chloro‐2‐butanol Méndez, Jonh J. Oromi, Mireia Cervero, Maria Balcells, Mercè Torres, Mercè Canela, Ramon 2006 http://dx.doi.org/10.1002/chir.20339 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fchir.20339 https://onlinelibrary.wiley.com/doi/pdf/10.1002/chir.20339 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor Chirality volume 19, issue 1, page 44-50 ISSN 0899-0042 1520-636X journal-article 2006 crwiley https://doi.org/10.1002/chir.20339 2024-05-31T08:15:38Z Abstract Preparation of 98% ee ( R )‐4‐chloro‐2‐butanol was carried out by the enzymatic hydrolysis of chlorohydrin esters, using fungal resting cells and commercial enzymes. Hydrolyzes were carried out using lipases from Candida antarctica (Novozym 435®), C. rugosa, Rhizomucor miehei (Lipozyme® IM), Burkolia cepacia , and resting cells of Rhizopus oryzae and Aspergillus flavus . The influence of the enzyme, the solvent, the temperature, and the alkyl chain length on the selectivity of hydrolyzes of isomeric mixtures of chlorohydrin esters is described. Regioselectivity was higher than 95% for some of the tested lipases. Novozym 435 allowed preparation of the ( R )‐4‐chloro‐2‐butanol after 15 min of reaction at 30–40°C. Chirality, 2006. © 2006 Wiley‐Liss, Inc. Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library Rugosa ENVELOPE(-61.250,-61.250,-62.633,-62.633) Chirality 19 1 44 50 |
institution |
Open Polar |
collection |
Wiley Online Library |
op_collection_id |
crwiley |
language |
English |
description |
Abstract Preparation of 98% ee ( R )‐4‐chloro‐2‐butanol was carried out by the enzymatic hydrolysis of chlorohydrin esters, using fungal resting cells and commercial enzymes. Hydrolyzes were carried out using lipases from Candida antarctica (Novozym 435®), C. rugosa, Rhizomucor miehei (Lipozyme® IM), Burkolia cepacia , and resting cells of Rhizopus oryzae and Aspergillus flavus . The influence of the enzyme, the solvent, the temperature, and the alkyl chain length on the selectivity of hydrolyzes of isomeric mixtures of chlorohydrin esters is described. Regioselectivity was higher than 95% for some of the tested lipases. Novozym 435 allowed preparation of the ( R )‐4‐chloro‐2‐butanol after 15 min of reaction at 30–40°C. Chirality, 2006. © 2006 Wiley‐Liss, Inc. |
format |
Article in Journal/Newspaper |
author |
Méndez, Jonh J. Oromi, Mireia Cervero, Maria Balcells, Mercè Torres, Mercè Canela, Ramon |
spellingShingle |
Méndez, Jonh J. Oromi, Mireia Cervero, Maria Balcells, Mercè Torres, Mercè Canela, Ramon Combining regio‐ and enantioselectivity of lipases for the preparation of ( R)‐4‐chloro‐2‐butanol |
author_facet |
Méndez, Jonh J. Oromi, Mireia Cervero, Maria Balcells, Mercè Torres, Mercè Canela, Ramon |
author_sort |
Méndez, Jonh J. |
title |
Combining regio‐ and enantioselectivity of lipases for the preparation of ( R)‐4‐chloro‐2‐butanol |
title_short |
Combining regio‐ and enantioselectivity of lipases for the preparation of ( R)‐4‐chloro‐2‐butanol |
title_full |
Combining regio‐ and enantioselectivity of lipases for the preparation of ( R)‐4‐chloro‐2‐butanol |
title_fullStr |
Combining regio‐ and enantioselectivity of lipases for the preparation of ( R)‐4‐chloro‐2‐butanol |
title_full_unstemmed |
Combining regio‐ and enantioselectivity of lipases for the preparation of ( R)‐4‐chloro‐2‐butanol |
title_sort |
combining regio‐ and enantioselectivity of lipases for the preparation of ( r)‐4‐chloro‐2‐butanol |
publisher |
Wiley |
publishDate |
2006 |
url |
http://dx.doi.org/10.1002/chir.20339 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fchir.20339 https://onlinelibrary.wiley.com/doi/pdf/10.1002/chir.20339 |
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 |
Chirality volume 19, issue 1, page 44-50 ISSN 0899-0042 1520-636X |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1002/chir.20339 |
container_title |
Chirality |
container_volume |
19 |
container_issue |
1 |
container_start_page |
44 |
op_container_end_page |
50 |
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1802651866189791232 |