Regioselective Synthesis of Lactulose Esters by Candida antarctica and Thermomyces lanuginosus Lipases
The interest in sugar esters as emulsifiers has been increasing in recent years because they have tunable surfactant properties that depend on the chain length of the fatty acid and the type of the sugar, covering a wide range of hydrophilic-lipophilic balance (HLB). In this work, ten biocatalysts w...
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ftdoajarticles:oai:doaj.org/article:b45549be8534426b8ead71c3f5ac11f1 2023-05-15T13:59:44+02:00 Regioselective Synthesis of Lactulose Esters by Candida antarctica and Thermomyces lanuginosus Lipases Luis F. Chávez-Flores Hiram Isaac Beltran Daniel Arrieta-Baez Dolores Reyes-Duarte 2017-09-01T00:00:00Z https://doi.org/10.3390/catal7090263 https://doaj.org/article/b45549be8534426b8ead71c3f5ac11f1 EN eng MDPI AG https://www.mdpi.com/2073-4344/7/9/263 https://doaj.org/toc/2073-4344 2073-4344 doi:10.3390/catal7090263 https://doaj.org/article/b45549be8534426b8ead71c3f5ac11f1 Catalysts, Vol 7, Iss 9, p 263 (2017) biocatalysts lipases lactulose prebiotic sugar sugar fatty acid esters transesterification regioselectivity Chemical technology TP1-1185 Chemistry QD1-999 article 2017 ftdoajarticles https://doi.org/10.3390/catal7090263 2022-12-31T03:42:48Z The interest in sugar esters as emulsifiers has been increasing in recent years because they have tunable surfactant properties that depend on the chain length of the fatty acid and the type of the sugar, covering a wide range of hydrophilic-lipophilic balance (HLB). In this work, ten biocatalysts were used for the transesterification reaction screening of lactulose, a prebiotic sugar, with vinyl laurate. The reactions were followed by thin layer chromatography (TLC) analysis, identifying two major monoesters mixtures defined as monoester fraction 1 and monoester fraction 2. Candida antarctica lipase B (Novozym 435) produces “monoester fraction 1”, while Thermomyces lanuginosus lipase (Lipozyme® TL IM) and Mucor miehei lipase (Lipozyme®) seem to produce the same “monoester fraction 2”. These three enzymes were selected as model biocatalysts for a kinetic study, and monoester fractions 1 and 2 from Novozym 435 and Lipozyme® TL IM, respectively, were used for product characterization. Monoester fraction 1 contained 86.9% of the major monoester in position 1-O-, and monoester fraction 2 contained 91.4% of 6′-O-. Although these lipases acylated three positions of lactulose, they mainly synthesize a monoester presenting regioselectivity. These results contribute to the study of the chemical structure diversity of biosurfactants to enhance their applications in foods, pharmaceutical products, and cosmetics. Article in Journal/Newspaper Antarc* Antarctica Directory of Open Access Journals: DOAJ Articles Catalysts 7 9 263 |
institution |
Open Polar |
collection |
Directory of Open Access Journals: DOAJ Articles |
op_collection_id |
ftdoajarticles |
language |
English |
topic |
biocatalysts lipases lactulose prebiotic sugar sugar fatty acid esters transesterification regioselectivity Chemical technology TP1-1185 Chemistry QD1-999 |
spellingShingle |
biocatalysts lipases lactulose prebiotic sugar sugar fatty acid esters transesterification regioselectivity Chemical technology TP1-1185 Chemistry QD1-999 Luis F. Chávez-Flores Hiram Isaac Beltran Daniel Arrieta-Baez Dolores Reyes-Duarte Regioselective Synthesis of Lactulose Esters by Candida antarctica and Thermomyces lanuginosus Lipases |
topic_facet |
biocatalysts lipases lactulose prebiotic sugar sugar fatty acid esters transesterification regioselectivity Chemical technology TP1-1185 Chemistry QD1-999 |
description |
The interest in sugar esters as emulsifiers has been increasing in recent years because they have tunable surfactant properties that depend on the chain length of the fatty acid and the type of the sugar, covering a wide range of hydrophilic-lipophilic balance (HLB). In this work, ten biocatalysts were used for the transesterification reaction screening of lactulose, a prebiotic sugar, with vinyl laurate. The reactions were followed by thin layer chromatography (TLC) analysis, identifying two major monoesters mixtures defined as monoester fraction 1 and monoester fraction 2. Candida antarctica lipase B (Novozym 435) produces “monoester fraction 1”, while Thermomyces lanuginosus lipase (Lipozyme® TL IM) and Mucor miehei lipase (Lipozyme®) seem to produce the same “monoester fraction 2”. These three enzymes were selected as model biocatalysts for a kinetic study, and monoester fractions 1 and 2 from Novozym 435 and Lipozyme® TL IM, respectively, were used for product characterization. Monoester fraction 1 contained 86.9% of the major monoester in position 1-O-, and monoester fraction 2 contained 91.4% of 6′-O-. Although these lipases acylated three positions of lactulose, they mainly synthesize a monoester presenting regioselectivity. These results contribute to the study of the chemical structure diversity of biosurfactants to enhance their applications in foods, pharmaceutical products, and cosmetics. |
format |
Article in Journal/Newspaper |
author |
Luis F. Chávez-Flores Hiram Isaac Beltran Daniel Arrieta-Baez Dolores Reyes-Duarte |
author_facet |
Luis F. Chávez-Flores Hiram Isaac Beltran Daniel Arrieta-Baez Dolores Reyes-Duarte |
author_sort |
Luis F. Chávez-Flores |
title |
Regioselective Synthesis of Lactulose Esters by Candida antarctica and Thermomyces lanuginosus Lipases |
title_short |
Regioselective Synthesis of Lactulose Esters by Candida antarctica and Thermomyces lanuginosus Lipases |
title_full |
Regioselective Synthesis of Lactulose Esters by Candida antarctica and Thermomyces lanuginosus Lipases |
title_fullStr |
Regioselective Synthesis of Lactulose Esters by Candida antarctica and Thermomyces lanuginosus Lipases |
title_full_unstemmed |
Regioselective Synthesis of Lactulose Esters by Candida antarctica and Thermomyces lanuginosus Lipases |
title_sort |
regioselective synthesis of lactulose esters by candida antarctica and thermomyces lanuginosus lipases |
publisher |
MDPI AG |
publishDate |
2017 |
url |
https://doi.org/10.3390/catal7090263 https://doaj.org/article/b45549be8534426b8ead71c3f5ac11f1 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Catalysts, Vol 7, Iss 9, p 263 (2017) |
op_relation |
https://www.mdpi.com/2073-4344/7/9/263 https://doaj.org/toc/2073-4344 2073-4344 doi:10.3390/catal7090263 https://doaj.org/article/b45549be8534426b8ead71c3f5ac11f1 |
op_doi |
https://doi.org/10.3390/catal7090263 |
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Catalysts |
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