Regioselective synthesis of 6’’- O -lauroyl-1-kestose and 6’’’- O -lauroylnystose by sequential enzymatic reactions of transfructosylation and acylation
Fructan fatty acid esters are amphiphilic compounds with potential applications in the food industry due to their surface-active properties on the air/water interface. In this work, the regioselective synthesis of fatty acid esters of short-chain inulin-type fructooligosaccharides (FOS) was carried...
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Taylor & Francis
2021
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ftdatacite:10.6084/m9.figshare.14995030.v1 2023-05-15T14:01:55+02:00 Regioselective synthesis of 6’’- O -lauroyl-1-kestose and 6’’’- O -lauroylnystose by sequential enzymatic reactions of transfructosylation and acylation Campos-Valdez, Amador Roberto Casas-Godoy, Leticia Sandoval, Georgina Hernández, Lázaro Sassaki, Guilherme Lanzi de Menezes, Leociley Rocha Alencar Campos-Terán, José Reyes-Duarte, Dolores Arrizon, Javier 2021 https://dx.doi.org/10.6084/m9.figshare.14995030.v1 https://tandf.figshare.com/articles/journal_contribution/Regioselective_synthesis_of_6_-_i_O_i_-lauroyl-1-kestose_and_6__-_i_O_i_-lauroylnystose_by_sequential_enzymatic_reactions_of_transfructosylation_and_acylation/14995030/1 unknown Taylor & Francis https://dx.doi.org/10.1080/10242422.2021.1952192 https://dx.doi.org/10.6084/m9.figshare.14995030 Creative Commons Attribution 4.0 International https://creativecommons.org/licenses/by/4.0/legalcode cc-by-4.0 CC-BY Biochemistry 29999 Physical Sciences not elsewhere classified FOS Physical sciences Microbiology FOS Biological sciences Cell Biology Genetics Biotechnology 59999 Environmental Sciences not elsewhere classified FOS Earth and related environmental sciences 39999 Chemical Sciences not elsewhere classified FOS Chemical sciences article-journal ScholarlyArticle Journal contribution Text 2021 ftdatacite https://doi.org/10.6084/m9.figshare.14995030.v1 https://doi.org/10.1080/10242422.2021.1952192 https://doi.org/10.6084/m9.figshare.14995030 2022-04-01T17:52:11Z Fructan fatty acid esters are amphiphilic compounds with potential applications in the food industry due to their surface-active properties on the air/water interface. In this work, the regioselective synthesis of fatty acid esters of short-chain inulin-type fructooligosaccharides (FOS) was carried out in a two-step process comprising sequential enzymatic reactions of transfructosylation and acylation. In the first step, Schedonorus arundinaceus sucrose:sucrose 1-fructosyltransferase (1-SST, EC 2.4.1.99) converted sucrose (600 g/L) into the trisaccharide 1-kestose and the tetrasaccharide nystose in a ratio 9:1 with their sum accounting for 53% (w/w) of total carbohydrates. In the second step, the FOS mixture was transesterified with vinyl laurate in 2-methyl-2-butanol by immobilized Candida antarctica lipase B (CALB) (EC.3.1.1.3). NMR analysis of the synthesized monolaurate FOS esters revealed a regioselective acylation of the 6-OH of the terminal fructosyl moiety of both 1-kestose and nystose. The hydrophilic-lipophilic balance (HLB) values of 6’’- O -lauroyl-1-kestose and 6’’’- O -lauroylnystose were 14.7 and 15.7, respectively; which suggests their use as oil in water (O/W) emulsifiers. The main compound 6’’- O -lauroyl-1-kestose with critical micelle concentration (CMC) of 0.6 mM and surface tension of 45.8 mN/m proved to be a more efficient surfactant than 6’’’- O -lauroylnystose (CMC 5.38 mM) and surface tension 36.26 mN/m). We report a regioselective method for the synthesis of lauryl-FOS using the abundant and renewable resource sucrose as the starting substrate. Text Antarc* Antarctica DataCite Metadata Store (German National Library of Science and Technology) |
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topic |
Biochemistry 29999 Physical Sciences not elsewhere classified FOS Physical sciences Microbiology FOS Biological sciences Cell Biology Genetics Biotechnology 59999 Environmental Sciences not elsewhere classified FOS Earth and related environmental sciences 39999 Chemical Sciences not elsewhere classified FOS Chemical sciences |
spellingShingle |
Biochemistry 29999 Physical Sciences not elsewhere classified FOS Physical sciences Microbiology FOS Biological sciences Cell Biology Genetics Biotechnology 59999 Environmental Sciences not elsewhere classified FOS Earth and related environmental sciences 39999 Chemical Sciences not elsewhere classified FOS Chemical sciences Campos-Valdez, Amador Roberto Casas-Godoy, Leticia Sandoval, Georgina Hernández, Lázaro Sassaki, Guilherme Lanzi de Menezes, Leociley Rocha Alencar Campos-Terán, José Reyes-Duarte, Dolores Arrizon, Javier Regioselective synthesis of 6’’- O -lauroyl-1-kestose and 6’’’- O -lauroylnystose by sequential enzymatic reactions of transfructosylation and acylation |
topic_facet |
Biochemistry 29999 Physical Sciences not elsewhere classified FOS Physical sciences Microbiology FOS Biological sciences Cell Biology Genetics Biotechnology 59999 Environmental Sciences not elsewhere classified FOS Earth and related environmental sciences 39999 Chemical Sciences not elsewhere classified FOS Chemical sciences |
description |
Fructan fatty acid esters are amphiphilic compounds with potential applications in the food industry due to their surface-active properties on the air/water interface. In this work, the regioselective synthesis of fatty acid esters of short-chain inulin-type fructooligosaccharides (FOS) was carried out in a two-step process comprising sequential enzymatic reactions of transfructosylation and acylation. In the first step, Schedonorus arundinaceus sucrose:sucrose 1-fructosyltransferase (1-SST, EC 2.4.1.99) converted sucrose (600 g/L) into the trisaccharide 1-kestose and the tetrasaccharide nystose in a ratio 9:1 with their sum accounting for 53% (w/w) of total carbohydrates. In the second step, the FOS mixture was transesterified with vinyl laurate in 2-methyl-2-butanol by immobilized Candida antarctica lipase B (CALB) (EC.3.1.1.3). NMR analysis of the synthesized monolaurate FOS esters revealed a regioselective acylation of the 6-OH of the terminal fructosyl moiety of both 1-kestose and nystose. The hydrophilic-lipophilic balance (HLB) values of 6’’- O -lauroyl-1-kestose and 6’’’- O -lauroylnystose were 14.7 and 15.7, respectively; which suggests their use as oil in water (O/W) emulsifiers. The main compound 6’’- O -lauroyl-1-kestose with critical micelle concentration (CMC) of 0.6 mM and surface tension of 45.8 mN/m proved to be a more efficient surfactant than 6’’’- O -lauroylnystose (CMC 5.38 mM) and surface tension 36.26 mN/m). We report a regioselective method for the synthesis of lauryl-FOS using the abundant and renewable resource sucrose as the starting substrate. |
format |
Text |
author |
Campos-Valdez, Amador Roberto Casas-Godoy, Leticia Sandoval, Georgina Hernández, Lázaro Sassaki, Guilherme Lanzi de Menezes, Leociley Rocha Alencar Campos-Terán, José Reyes-Duarte, Dolores Arrizon, Javier |
author_facet |
Campos-Valdez, Amador Roberto Casas-Godoy, Leticia Sandoval, Georgina Hernández, Lázaro Sassaki, Guilherme Lanzi de Menezes, Leociley Rocha Alencar Campos-Terán, José Reyes-Duarte, Dolores Arrizon, Javier |
author_sort |
Campos-Valdez, Amador Roberto |
title |
Regioselective synthesis of 6’’- O -lauroyl-1-kestose and 6’’’- O -lauroylnystose by sequential enzymatic reactions of transfructosylation and acylation |
title_short |
Regioselective synthesis of 6’’- O -lauroyl-1-kestose and 6’’’- O -lauroylnystose by sequential enzymatic reactions of transfructosylation and acylation |
title_full |
Regioselective synthesis of 6’’- O -lauroyl-1-kestose and 6’’’- O -lauroylnystose by sequential enzymatic reactions of transfructosylation and acylation |
title_fullStr |
Regioselective synthesis of 6’’- O -lauroyl-1-kestose and 6’’’- O -lauroylnystose by sequential enzymatic reactions of transfructosylation and acylation |
title_full_unstemmed |
Regioselective synthesis of 6’’- O -lauroyl-1-kestose and 6’’’- O -lauroylnystose by sequential enzymatic reactions of transfructosylation and acylation |
title_sort |
regioselective synthesis of 6’’- o -lauroyl-1-kestose and 6’’’- o -lauroylnystose by sequential enzymatic reactions of transfructosylation and acylation |
publisher |
Taylor & Francis |
publishDate |
2021 |
url |
https://dx.doi.org/10.6084/m9.figshare.14995030.v1 https://tandf.figshare.com/articles/journal_contribution/Regioselective_synthesis_of_6_-_i_O_i_-lauroyl-1-kestose_and_6__-_i_O_i_-lauroylnystose_by_sequential_enzymatic_reactions_of_transfructosylation_and_acylation/14995030/1 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
https://dx.doi.org/10.1080/10242422.2021.1952192 https://dx.doi.org/10.6084/m9.figshare.14995030 |
op_rights |
Creative Commons Attribution 4.0 International https://creativecommons.org/licenses/by/4.0/legalcode cc-by-4.0 |
op_rightsnorm |
CC-BY |
op_doi |
https://doi.org/10.6084/m9.figshare.14995030.v1 https://doi.org/10.1080/10242422.2021.1952192 https://doi.org/10.6084/m9.figshare.14995030 |
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1766271980131057664 |