Regioselective Hydrolysis of Different Peracetylated β‐Monosaccharides by Immobilized Lipases from Different Sources. Key Role of The Immobilization
Abstract The effect of the immobilization strategy on the activity, specificity and regioselectivity of three different lipases [those from Thermomyces lanuginose (TLL) , Aspergillus niger (ANL) and Candida antarctica B (CAL‐B)] in the hydrolysis of peracetylated β‐monosaccharides has been evaluated...
Published in: | Advanced Synthesis & Catalysis |
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Online Access: | http://dx.doi.org/10.1002/adsc.200700055 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fadsc.200700055 https://onlinelibrary.wiley.com/doi/pdf/10.1002/adsc.200700055 |
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crwiley:10.1002/adsc.200700055 2024-06-02T07:57:08+00:00 Regioselective Hydrolysis of Different Peracetylated β‐Monosaccharides by Immobilized Lipases from Different Sources. Key Role of The Immobilization Palomo, Jose M. Filice, Marco Fernandez‐Lafuente, Roberto Terreni, Marco Guisan, Jose M. 2007 http://dx.doi.org/10.1002/adsc.200700055 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fadsc.200700055 https://onlinelibrary.wiley.com/doi/pdf/10.1002/adsc.200700055 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor Advanced Synthesis & Catalysis volume 349, issue 11-12, page 1969-1976 ISSN 1615-4150 1615-4169 journal-article 2007 crwiley https://doi.org/10.1002/adsc.200700055 2024-05-03T10:35:08Z Abstract The effect of the immobilization strategy on the activity, specificity and regioselectivity of three different lipases [those from Thermomyces lanuginose (TLL) , Aspergillus niger (ANL) and Candida antarctica B (CAL‐B)] in the hydrolysis of peracetylated β‐monosaccharides has been evaluated. Three very different immobilization strategies were utilized, covalent attachment, anionic exchange and interfacial activation on a hydrophobic support. The octyl‐TLL immobilized preparation was the most efficient biocatalyst in the hydrolysis of 1,2,3,4,6‐penta‐ O ‐acetyl‐β‐ D ‐galactopyranose, producing specifically 6‐hydroxy‐1,2,3,4‐tetra‐ O ‐acetyl‐β‐ D ‐galactopyranose in 95 % overall yield, whereas the CNBr‐TLL preparation was 48 times slower and regioselective towards the anomeric position, producing the 1‐hydroxy derivative in 70 % yield. The PEI‐TLL immobilized preparation was the most efficient catalyzing the hydrolysis of 1,2,3,4,6‐penta‐ O ‐acetyl‐β‐ D ‐glucopyranose, permitting us to obtain up to 70 % of the 6‐hydroxy product. In the hydrolysis of 2‐acetamido‐2‐deoxy‐1,3,4,6‐tetra‐ O ‐acetyl‐β‐ D ‐glucopyranose, the octyl‐CALB preparation was not selective at all for the production of monohydroxy products whereas when CAL‐B was immobilized on PEI‐agarose, the enzyme was highly specific and regioselective producing the 6‐hydroxy‐2‐acetamido‐2‐deoxy‐1,3,4‐tri‐ O ‐acetyl‐β‐ D ‐glucopyranose in 70 % yield. Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library Advanced Synthesis & Catalysis 349 11-12 1969 1976 |
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Open Polar |
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Wiley Online Library |
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crwiley |
language |
English |
description |
Abstract The effect of the immobilization strategy on the activity, specificity and regioselectivity of three different lipases [those from Thermomyces lanuginose (TLL) , Aspergillus niger (ANL) and Candida antarctica B (CAL‐B)] in the hydrolysis of peracetylated β‐monosaccharides has been evaluated. Three very different immobilization strategies were utilized, covalent attachment, anionic exchange and interfacial activation on a hydrophobic support. The octyl‐TLL immobilized preparation was the most efficient biocatalyst in the hydrolysis of 1,2,3,4,6‐penta‐ O ‐acetyl‐β‐ D ‐galactopyranose, producing specifically 6‐hydroxy‐1,2,3,4‐tetra‐ O ‐acetyl‐β‐ D ‐galactopyranose in 95 % overall yield, whereas the CNBr‐TLL preparation was 48 times slower and regioselective towards the anomeric position, producing the 1‐hydroxy derivative in 70 % yield. The PEI‐TLL immobilized preparation was the most efficient catalyzing the hydrolysis of 1,2,3,4,6‐penta‐ O ‐acetyl‐β‐ D ‐glucopyranose, permitting us to obtain up to 70 % of the 6‐hydroxy product. In the hydrolysis of 2‐acetamido‐2‐deoxy‐1,3,4,6‐tetra‐ O ‐acetyl‐β‐ D ‐glucopyranose, the octyl‐CALB preparation was not selective at all for the production of monohydroxy products whereas when CAL‐B was immobilized on PEI‐agarose, the enzyme was highly specific and regioselective producing the 6‐hydroxy‐2‐acetamido‐2‐deoxy‐1,3,4‐tri‐ O ‐acetyl‐β‐ D ‐glucopyranose in 70 % yield. |
format |
Article in Journal/Newspaper |
author |
Palomo, Jose M. Filice, Marco Fernandez‐Lafuente, Roberto Terreni, Marco Guisan, Jose M. |
spellingShingle |
Palomo, Jose M. Filice, Marco Fernandez‐Lafuente, Roberto Terreni, Marco Guisan, Jose M. Regioselective Hydrolysis of Different Peracetylated β‐Monosaccharides by Immobilized Lipases from Different Sources. Key Role of The Immobilization |
author_facet |
Palomo, Jose M. Filice, Marco Fernandez‐Lafuente, Roberto Terreni, Marco Guisan, Jose M. |
author_sort |
Palomo, Jose M. |
title |
Regioselective Hydrolysis of Different Peracetylated β‐Monosaccharides by Immobilized Lipases from Different Sources. Key Role of The Immobilization |
title_short |
Regioselective Hydrolysis of Different Peracetylated β‐Monosaccharides by Immobilized Lipases from Different Sources. Key Role of The Immobilization |
title_full |
Regioselective Hydrolysis of Different Peracetylated β‐Monosaccharides by Immobilized Lipases from Different Sources. Key Role of The Immobilization |
title_fullStr |
Regioselective Hydrolysis of Different Peracetylated β‐Monosaccharides by Immobilized Lipases from Different Sources. Key Role of The Immobilization |
title_full_unstemmed |
Regioselective Hydrolysis of Different Peracetylated β‐Monosaccharides by Immobilized Lipases from Different Sources. Key Role of The Immobilization |
title_sort |
regioselective hydrolysis of different peracetylated β‐monosaccharides by immobilized lipases from different sources. key role of the immobilization |
publisher |
Wiley |
publishDate |
2007 |
url |
http://dx.doi.org/10.1002/adsc.200700055 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fadsc.200700055 https://onlinelibrary.wiley.com/doi/pdf/10.1002/adsc.200700055 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Advanced Synthesis & Catalysis volume 349, issue 11-12, page 1969-1976 ISSN 1615-4150 1615-4169 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1002/adsc.200700055 |
container_title |
Advanced Synthesis & Catalysis |
container_volume |
349 |
container_issue |
11-12 |
container_start_page |
1969 |
op_container_end_page |
1976 |
_version_ |
1800739022993096704 |