Production and Digestibility Studies of β-Galactosyl Xylitol Derivatives Using Heterogeneous Catalysts of LacA β-Galactosidase from <i>Lactobacillus Plantarum</i> WCFS1

The synthesis of β-galactosyl xylitol derivatives using immobilized LacA β-galactosidase from <i>Lactobacillus plantarum</i> WCFS1 is presented. These compounds have the potential to replace traditional sugars by their properties as sweetener and taking the advantages of a low digestibil...

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Main Authors: Eduardo Rosado, Paloma Delgado-Fernández, Blanca de las Rivas, Rosario Muñoz, Francisco Javier Moreno, Nieves Corzo, Cesar Mateo
Format: Article
Language:English
Published: MDPI AG 2022-02-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/27/4/1235
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author Eduardo Rosado
Paloma Delgado-Fernández
Blanca de las Rivas
Rosario Muñoz
Francisco Javier Moreno
Nieves Corzo
Cesar Mateo
author_facet Eduardo Rosado
Paloma Delgado-Fernández
Blanca de las Rivas
Rosario Muñoz
Francisco Javier Moreno
Nieves Corzo
Cesar Mateo
author_sort Eduardo Rosado
collection DOAJ
description The synthesis of β-galactosyl xylitol derivatives using immobilized LacA β-galactosidase from <i>Lactobacillus plantarum</i> WCFS1 is presented. These compounds have the potential to replace traditional sugars by their properties as sweetener and taking the advantages of a low digestibility. The enzyme was immobilized on different supports, obtaining immobilized preparations with different activity and stability. The immobilization on agarose-IDA-Zn-CHO in the presence of galactose allowed for the conserving of 78% of the offered activity. This preparation was 3.8 times more stable than soluble. Since the enzyme has polyhistidine tags, this support allowed the immobilization, purification and stabilization in one step. The immobilized preparation was used in synthesis obtaining two main products and a total of around 68 g/L of β-galactosyl xylitol derivatives and improving the synthesis/hydrolysis ratio by around 30% compared to that of the soluble enzyme. The catalyst was recycled 10 times, preserving an activity higher than 50%. The in vitro intestinal digestibility of the main β-galactosyl xylitol derivatives was lower than that of lactose, being around 6 and 15% for the galacto-xylitol derivatives compared to 55% of lactose after 120 min of digestion. The optimal amount immobilized constitutes a very useful tool to synthetize β-galactosyl xylitol derivatives since it can be used as a catalyst with high yield and being recycled for at least 10 more cycles.
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spelling doaj.art-4683618f73f14a28917f04a5611597dd2023-11-23T21:20:53ZengMDPI AGMolecules1420-30492022-02-01274123510.3390/molecules27041235Production and Digestibility Studies of β-Galactosyl Xylitol Derivatives Using Heterogeneous Catalysts of LacA β-Galactosidase from <i>Lactobacillus Plantarum</i> WCFS1Eduardo Rosado0Paloma Delgado-Fernández1Blanca de las Rivas2Rosario Muñoz3Francisco Javier Moreno4Nieves Corzo5Cesar Mateo6Departamento de Biocátalisis, Instituto de Catálisis y Petroleoquímica, CSIC, Marie Curie 2, 28049 Madrid, SpainDepartamento de Bioactividad y Análisis de Alimentos, Instituto de Investigación en Ciencias de la Alimentación, CIAL (CSIC-UAM), Nicolás Cabrera 9, 28049 Madrid, SpainInstituto de Ciencia y Tecnología de Alimentos y Nutrición, ICTAN (CSIC), Juan de la Cierva 3, 28006 Madrid, SpainInstituto de Ciencia y Tecnología de Alimentos y Nutrición, ICTAN (CSIC), Juan de la Cierva 3, 28006 Madrid, SpainDepartamento de Bioactividad y Análisis de Alimentos, Instituto de Investigación en Ciencias de la Alimentación, CIAL (CSIC-UAM), Nicolás Cabrera 9, 28049 Madrid, SpainDepartamento de Bioactividad y Análisis de Alimentos, Instituto de Investigación en Ciencias de la Alimentación, CIAL (CSIC-UAM), Nicolás Cabrera 9, 28049 Madrid, SpainDepartamento de Biocátalisis, Instituto de Catálisis y Petroleoquímica, CSIC, Marie Curie 2, 28049 Madrid, SpainThe synthesis of β-galactosyl xylitol derivatives using immobilized LacA β-galactosidase from <i>Lactobacillus plantarum</i> WCFS1 is presented. These compounds have the potential to replace traditional sugars by their properties as sweetener and taking the advantages of a low digestibility. The enzyme was immobilized on different supports, obtaining immobilized preparations with different activity and stability. The immobilization on agarose-IDA-Zn-CHO in the presence of galactose allowed for the conserving of 78% of the offered activity. This preparation was 3.8 times more stable than soluble. Since the enzyme has polyhistidine tags, this support allowed the immobilization, purification and stabilization in one step. The immobilized preparation was used in synthesis obtaining two main products and a total of around 68 g/L of β-galactosyl xylitol derivatives and improving the synthesis/hydrolysis ratio by around 30% compared to that of the soluble enzyme. The catalyst was recycled 10 times, preserving an activity higher than 50%. The in vitro intestinal digestibility of the main β-galactosyl xylitol derivatives was lower than that of lactose, being around 6 and 15% for the galacto-xylitol derivatives compared to 55% of lactose after 120 min of digestion. The optimal amount immobilized constitutes a very useful tool to synthetize β-galactosyl xylitol derivatives since it can be used as a catalyst with high yield and being recycled for at least 10 more cycles.https://www.mdpi.com/1420-3049/27/4/1235galactosyl xylitolgalactooligosaccharidesβ-galactosidase<i>Lactobacillus plantarum</i>enzyme immobilizationdigestibility
spellingShingle Eduardo Rosado
Paloma Delgado-Fernández
Blanca de las Rivas
Rosario Muñoz
Francisco Javier Moreno
Nieves Corzo
Cesar Mateo
Production and Digestibility Studies of β-Galactosyl Xylitol Derivatives Using Heterogeneous Catalysts of LacA β-Galactosidase from <i>Lactobacillus Plantarum</i> WCFS1
Molecules
galactosyl xylitol
galactooligosaccharides
β-galactosidase
<i>Lactobacillus plantarum</i>
enzyme immobilization
digestibility
title Production and Digestibility Studies of β-Galactosyl Xylitol Derivatives Using Heterogeneous Catalysts of LacA β-Galactosidase from <i>Lactobacillus Plantarum</i> WCFS1
title_full Production and Digestibility Studies of β-Galactosyl Xylitol Derivatives Using Heterogeneous Catalysts of LacA β-Galactosidase from <i>Lactobacillus Plantarum</i> WCFS1
title_fullStr Production and Digestibility Studies of β-Galactosyl Xylitol Derivatives Using Heterogeneous Catalysts of LacA β-Galactosidase from <i>Lactobacillus Plantarum</i> WCFS1
title_full_unstemmed Production and Digestibility Studies of β-Galactosyl Xylitol Derivatives Using Heterogeneous Catalysts of LacA β-Galactosidase from <i>Lactobacillus Plantarum</i> WCFS1
title_short Production and Digestibility Studies of β-Galactosyl Xylitol Derivatives Using Heterogeneous Catalysts of LacA β-Galactosidase from <i>Lactobacillus Plantarum</i> WCFS1
title_sort production and digestibility studies of β galactosyl xylitol derivatives using heterogeneous catalysts of laca β galactosidase from i lactobacillus plantarum i wcfs1
topic galactosyl xylitol
galactooligosaccharides
β-galactosidase
<i>Lactobacillus plantarum</i>
enzyme immobilization
digestibility
url https://www.mdpi.com/1420-3049/27/4/1235
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