Modulation of Immobilized Lipase Enantioselectivity via Chemical Amination
Abstract The aspartic and glutamic carboxylic groups of the surface of three different immobilized lipases (those from Candida antarctica (form B) (CAL‐B), Thermomyces lanuginose (TLL) and Pseudomonas fluorescens (PFL) have been modified with ethylenediamine (after activation of the carboxylic funct...
Published in: | Advanced Synthesis & Catalysis |
---|---|
Main Authors: | , , , |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
Wiley
2007
|
Subjects: | |
Online Access: | http://dx.doi.org/10.1002/adsc.200600555 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fadsc.200600555 https://onlinelibrary.wiley.com/doi/pdf/10.1002/adsc.200600555 |
id |
crwiley:10.1002/adsc.200600555 |
---|---|
record_format |
openpolar |
spelling |
crwiley:10.1002/adsc.200600555 2024-09-09T19:10:16+00:00 Modulation of Immobilized Lipase Enantioselectivity via Chemical Amination Palomo, Jose M. Fernández‐Lorente, Gloria Guisán, Jose M. Fernández‐Lafuente, Roberto 2007 http://dx.doi.org/10.1002/adsc.200600555 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fadsc.200600555 https://onlinelibrary.wiley.com/doi/pdf/10.1002/adsc.200600555 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor Advanced Synthesis & Catalysis volume 349, issue 7, page 1119-1127 ISSN 1615-4150 1615-4169 journal-article 2007 crwiley https://doi.org/10.1002/adsc.200600555 2024-08-13T04:12:47Z Abstract The aspartic and glutamic carboxylic groups of the surface of three different immobilized lipases (those from Candida antarctica (form B) (CAL‐B), Thermomyces lanuginose (TLL) and Pseudomonas fluorescens (PFL) have been modified with ethylenediamine (after activation of the carboxylic function with carbodiimide). The exchange of groups with a negative charge for positively charged groups permitted us to greatly alter the activity, specificity and stereoselectivity of the lipase. Thus, in some cases, the activity of the lipases increased after the chemical modification while in other cases the activity was strongly reduced. Moreover, the effect of the experimental conditions on the activity was also strongly altered. Remarkably, the enantioselectivity of the enzymes in the hydrolysis of different mandelic acid derivatives was strongly modulated. For example, amination of the CNBr‐CAL‐B preparation greatly increased the enantioselectivity of the enzyme in the hydrolysis of (±)‐2‐hydroxyphenylacetic acid methyl ester, from an E value of 2 without modification up to E>100, affording ( R )‐mandelic acid in high purity ( ee >99 % at 50 % conversion) at pH 7 and 4 °C. Thus, the chemical modification of lipases seems to be a very powerful tool to improve their performance as enantioselective biocatalysts. Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library Advanced Synthesis & Catalysis 349 7 1119 1127 |
institution |
Open Polar |
collection |
Wiley Online Library |
op_collection_id |
crwiley |
language |
English |
description |
Abstract The aspartic and glutamic carboxylic groups of the surface of three different immobilized lipases (those from Candida antarctica (form B) (CAL‐B), Thermomyces lanuginose (TLL) and Pseudomonas fluorescens (PFL) have been modified with ethylenediamine (after activation of the carboxylic function with carbodiimide). The exchange of groups with a negative charge for positively charged groups permitted us to greatly alter the activity, specificity and stereoselectivity of the lipase. Thus, in some cases, the activity of the lipases increased after the chemical modification while in other cases the activity was strongly reduced. Moreover, the effect of the experimental conditions on the activity was also strongly altered. Remarkably, the enantioselectivity of the enzymes in the hydrolysis of different mandelic acid derivatives was strongly modulated. For example, amination of the CNBr‐CAL‐B preparation greatly increased the enantioselectivity of the enzyme in the hydrolysis of (±)‐2‐hydroxyphenylacetic acid methyl ester, from an E value of 2 without modification up to E>100, affording ( R )‐mandelic acid in high purity ( ee >99 % at 50 % conversion) at pH 7 and 4 °C. Thus, the chemical modification of lipases seems to be a very powerful tool to improve their performance as enantioselective biocatalysts. |
format |
Article in Journal/Newspaper |
author |
Palomo, Jose M. Fernández‐Lorente, Gloria Guisán, Jose M. Fernández‐Lafuente, Roberto |
spellingShingle |
Palomo, Jose M. Fernández‐Lorente, Gloria Guisán, Jose M. Fernández‐Lafuente, Roberto Modulation of Immobilized Lipase Enantioselectivity via Chemical Amination |
author_facet |
Palomo, Jose M. Fernández‐Lorente, Gloria Guisán, Jose M. Fernández‐Lafuente, Roberto |
author_sort |
Palomo, Jose M. |
title |
Modulation of Immobilized Lipase Enantioselectivity via Chemical Amination |
title_short |
Modulation of Immobilized Lipase Enantioselectivity via Chemical Amination |
title_full |
Modulation of Immobilized Lipase Enantioselectivity via Chemical Amination |
title_fullStr |
Modulation of Immobilized Lipase Enantioselectivity via Chemical Amination |
title_full_unstemmed |
Modulation of Immobilized Lipase Enantioselectivity via Chemical Amination |
title_sort |
modulation of immobilized lipase enantioselectivity via chemical amination |
publisher |
Wiley |
publishDate |
2007 |
url |
http://dx.doi.org/10.1002/adsc.200600555 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fadsc.200600555 https://onlinelibrary.wiley.com/doi/pdf/10.1002/adsc.200600555 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Advanced Synthesis & Catalysis volume 349, issue 7, page 1119-1127 ISSN 1615-4150 1615-4169 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1002/adsc.200600555 |
container_title |
Advanced Synthesis & Catalysis |
container_volume |
349 |
container_issue |
7 |
container_start_page |
1119 |
op_container_end_page |
1127 |
_version_ |
1809825046460366848 |