Regioselective hydrolysis of different peracetylated beta -monosaccharides by immobilized lipases from different sources. Key role of the immobilization
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 b-monosaccharides has been evaluated. Three ve...
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ftunivpavia:oai:iris.unipv.it:11571/135076 2023-11-12T04:06:43+01:00 Regioselective hydrolysis of different peracetylated beta -monosaccharides by immobilized lipases from different sources. Key role of the immobilization Palomo Jose M. Fernandez Lafuente Roberto Guisan Jose M. FILICE, MARCO TERRENI, MARCO Palomo Jose, M. Filice, Marco Fernandez Lafuente, Roberto Terreni, Marco Guisan Jose, M. 2007 STAMPA http://hdl.handle.net/11571/135076 eng eng volume:349 issue:11+12 firstpage:1969 lastpage:1976 journal:ADVANCED SYNTHESIS & CATALYSIS http://hdl.handle.net/11571/135076 Carbohydrate lipase immobilization info:eu-repo/semantics/article 2007 ftunivpavia 2023-10-30T21:26:21Z 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 b-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-beta-D-galactopyranose, producing specifically 6-hydroxy-1,2,3,4-tetra-O-acetyl-beta-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-beta-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-beta-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-beta-D-glucopyranose in 70% yield. Article in Journal/Newspaper Antarc* Antarctica IRIS UNIPV (Università degli studi di Pavia) |
institution |
Open Polar |
collection |
IRIS UNIPV (Università degli studi di Pavia) |
op_collection_id |
ftunivpavia |
language |
English |
topic |
Carbohydrate lipase immobilization |
spellingShingle |
Carbohydrate lipase immobilization Palomo Jose M. Fernandez Lafuente Roberto Guisan Jose M. FILICE, MARCO TERRENI, MARCO Regioselective hydrolysis of different peracetylated beta -monosaccharides by immobilized lipases from different sources. Key role of the immobilization |
topic_facet |
Carbohydrate lipase immobilization |
description |
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 b-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-beta-D-galactopyranose, producing specifically 6-hydroxy-1,2,3,4-tetra-O-acetyl-beta-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-beta-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-beta-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-beta-D-glucopyranose in 70% yield. |
author2 |
Palomo Jose, M. Filice, Marco Fernandez Lafuente, Roberto Terreni, Marco Guisan Jose, M. |
format |
Article in Journal/Newspaper |
author |
Palomo Jose M. Fernandez Lafuente Roberto Guisan Jose M. FILICE, MARCO TERRENI, MARCO |
author_facet |
Palomo Jose M. Fernandez Lafuente Roberto Guisan Jose M. FILICE, MARCO TERRENI, MARCO |
author_sort |
Palomo Jose M. |
title |
Regioselective hydrolysis of different peracetylated beta -monosaccharides by immobilized lipases from different sources. Key role of the immobilization |
title_short |
Regioselective hydrolysis of different peracetylated beta -monosaccharides by immobilized lipases from different sources. Key role of the immobilization |
title_full |
Regioselective hydrolysis of different peracetylated beta -monosaccharides by immobilized lipases from different sources. Key role of the immobilization |
title_fullStr |
Regioselective hydrolysis of different peracetylated beta -monosaccharides by immobilized lipases from different sources. Key role of the immobilization |
title_full_unstemmed |
Regioselective hydrolysis of different peracetylated beta -monosaccharides by immobilized lipases from different sources. Key role of the immobilization |
title_sort |
regioselective hydrolysis of different peracetylated beta -monosaccharides by immobilized lipases from different sources. key role of the immobilization |
publishDate |
2007 |
url |
http://hdl.handle.net/11571/135076 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
volume:349 issue:11+12 firstpage:1969 lastpage:1976 journal:ADVANCED SYNTHESIS & CATALYSIS http://hdl.handle.net/11571/135076 |
_version_ |
1782327735877632000 |