Biocatalytic acylation of sugar alcohols by 3-(4-hydroxyphenyl)propionic acid
Enzymatic synthesis of aromatic esters of four different sugar alcohols (xylitol, arabitol, mannitol, and sorbitol) with 3-(4-hydroxyphenyl)propionic acid was performed in organic solvent medium, using immobilized Candida antarctica lipase (Novozyme 435), and molecular sieves for control of the wate...
Published in: | Process Biochemistry |
---|---|
Main Authors: | , , , , |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
2012
|
Subjects: | |
Online Access: | https://research.wur.nl/en/publications/biocatalytic-acylation-of-sugar-alcohols-by-3-4-hydroxyphenylprop https://doi.org/10.1016/j.procbio.2012.06.015 |
id |
ftunivwagenin:oai:library.wur.nl:wurpubs/432615 |
---|---|
record_format |
openpolar |
spelling |
ftunivwagenin:oai:library.wur.nl:wurpubs/432615 2024-01-14T09:59:44+01:00 Biocatalytic acylation of sugar alcohols by 3-(4-hydroxyphenyl)propionic acid Croitoru, R. Fitigau, F. van den Broek, L.A.M. Frissen, A.E. Boeriu, C.G. 2012 application/pdf https://research.wur.nl/en/publications/biocatalytic-acylation-of-sugar-alcohols-by-3-4-hydroxyphenylprop https://doi.org/10.1016/j.procbio.2012.06.015 en eng https://edepot.wur.nl/243214 https://research.wur.nl/en/publications/biocatalytic-acylation-of-sugar-alcohols-by-3-4-hydroxyphenylprop doi:10.1016/j.procbio.2012.06.015 info:eu-repo/semantics/restrictedAccess Wageningen University & Research Process Biochemistry 47 (2012) 12 ISSN: 1359-5113 candida-antarctica lipase condensation copolyesters enzymatic preparation esters glycosides lipase-catalyzed esterification organic media phenolic-acids solvents info:eu-repo/semantics/article Article/Letter to editor info:eu-repo/semantics/publishedVersion 2012 ftunivwagenin https://doi.org/10.1016/j.procbio.2012.06.015 2023-12-20T23:18:35Z Enzymatic synthesis of aromatic esters of four different sugar alcohols (xylitol, arabitol, mannitol, and sorbitol) with 3-(4-hydroxyphenyl)propionic acid was performed in organic solvent medium, using immobilized Candida antarctica lipase (Novozyme 435), and molecular sieves for control of the water content. The influence of reaction parameters on the conversion has been investigated, including reaction time, temperature, alcohol/acid molar ratio, and enzyme amount. The highest conversions (94% for xylitol, 98% for arabitol, 80% for mannitol, and 93% for sorbitol) were obtained in pure tert-butanol at 60 °C and 72 h reaction time, 0.3 alcohol/acid molar ratio, and 0.5 g/mol enzyme/substrate ratio. The isolated new sugar alcohols esters were identified by different spectral analyses. MALDI-TOF MS analysis showed the formation of monoesters, diesters, and small quantities of triesters for all investigated sugar alcohols. The catalytic efficiency of the enzyme was higher for the pentitol substrates, decreasing in the following order: arabitol > xylitol > sorbitol > mannitol. These new compounds could have interesting applications in food, pharmaceutical and cosmetic formulations Article in Journal/Newspaper Antarc* Antarctica Wageningen UR (University & Research Centre): Digital Library Process Biochemistry 47 12 1894 1902 |
institution |
Open Polar |
collection |
Wageningen UR (University & Research Centre): Digital Library |
op_collection_id |
ftunivwagenin |
language |
English |
topic |
candida-antarctica lipase condensation copolyesters enzymatic preparation esters glycosides lipase-catalyzed esterification organic media phenolic-acids solvents |
spellingShingle |
candida-antarctica lipase condensation copolyesters enzymatic preparation esters glycosides lipase-catalyzed esterification organic media phenolic-acids solvents Croitoru, R. Fitigau, F. van den Broek, L.A.M. Frissen, A.E. Boeriu, C.G. Biocatalytic acylation of sugar alcohols by 3-(4-hydroxyphenyl)propionic acid |
topic_facet |
candida-antarctica lipase condensation copolyesters enzymatic preparation esters glycosides lipase-catalyzed esterification organic media phenolic-acids solvents |
description |
Enzymatic synthesis of aromatic esters of four different sugar alcohols (xylitol, arabitol, mannitol, and sorbitol) with 3-(4-hydroxyphenyl)propionic acid was performed in organic solvent medium, using immobilized Candida antarctica lipase (Novozyme 435), and molecular sieves for control of the water content. The influence of reaction parameters on the conversion has been investigated, including reaction time, temperature, alcohol/acid molar ratio, and enzyme amount. The highest conversions (94% for xylitol, 98% for arabitol, 80% for mannitol, and 93% for sorbitol) were obtained in pure tert-butanol at 60 °C and 72 h reaction time, 0.3 alcohol/acid molar ratio, and 0.5 g/mol enzyme/substrate ratio. The isolated new sugar alcohols esters were identified by different spectral analyses. MALDI-TOF MS analysis showed the formation of monoesters, diesters, and small quantities of triesters for all investigated sugar alcohols. The catalytic efficiency of the enzyme was higher for the pentitol substrates, decreasing in the following order: arabitol > xylitol > sorbitol > mannitol. These new compounds could have interesting applications in food, pharmaceutical and cosmetic formulations |
format |
Article in Journal/Newspaper |
author |
Croitoru, R. Fitigau, F. van den Broek, L.A.M. Frissen, A.E. Boeriu, C.G. |
author_facet |
Croitoru, R. Fitigau, F. van den Broek, L.A.M. Frissen, A.E. Boeriu, C.G. |
author_sort |
Croitoru, R. |
title |
Biocatalytic acylation of sugar alcohols by 3-(4-hydroxyphenyl)propionic acid |
title_short |
Biocatalytic acylation of sugar alcohols by 3-(4-hydroxyphenyl)propionic acid |
title_full |
Biocatalytic acylation of sugar alcohols by 3-(4-hydroxyphenyl)propionic acid |
title_fullStr |
Biocatalytic acylation of sugar alcohols by 3-(4-hydroxyphenyl)propionic acid |
title_full_unstemmed |
Biocatalytic acylation of sugar alcohols by 3-(4-hydroxyphenyl)propionic acid |
title_sort |
biocatalytic acylation of sugar alcohols by 3-(4-hydroxyphenyl)propionic acid |
publishDate |
2012 |
url |
https://research.wur.nl/en/publications/biocatalytic-acylation-of-sugar-alcohols-by-3-4-hydroxyphenylprop https://doi.org/10.1016/j.procbio.2012.06.015 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Process Biochemistry 47 (2012) 12 ISSN: 1359-5113 |
op_relation |
https://edepot.wur.nl/243214 https://research.wur.nl/en/publications/biocatalytic-acylation-of-sugar-alcohols-by-3-4-hydroxyphenylprop doi:10.1016/j.procbio.2012.06.015 |
op_rights |
info:eu-repo/semantics/restrictedAccess Wageningen University & Research |
op_doi |
https://doi.org/10.1016/j.procbio.2012.06.015 |
container_title |
Process Biochemistry |
container_volume |
47 |
container_issue |
12 |
container_start_page |
1894 |
op_container_end_page |
1902 |
_version_ |
1788060508625043456 |