Valorization of glycerol through the enzymatic synthesis of acylglycerides with high nutritional value

The production of specific acylglycerides from the selective esterification of glycerol is an attractive alternative for the valorization of this by-product of the biodiesel industry. In this way, products with high added value are generated, increasing the profitability of the overall process and r...

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Detalles Bibliográficos
Autores: Sanchez, Daniel Alberto, Tonetto, Gabriela Marta, Ferreira, María Luján
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2020
País:Argentina
Institución:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositorio:CONICET Digital (CONICET)
Idioma:inglés
OAI Identifier:oai:ri.conicet.gov.ar:11336/126853
Acceso en línea:http://hdl.handle.net/11336/126853
Access Level:acceso abierto
Palabra clave:ENZYMATIC ESTERIFICATION
FAT SUBSTITUTES
GLYCEROL VALORIZATION
NUTRITIONALLY VALUABLE ACYLGLYCERIDES
https://purl.org/becyt/ford/2.4
https://purl.org/becyt/ford/2
id AR_00a6940b456d2fead4873f7d4633b36b
oai_identifier_str oai:ri.conicet.gov.ar:11336/126853
network_acronym_str AR
network_name_str Argentina
repository_id_str
dc.title.none.fl_str_mv Valorization of glycerol through the enzymatic synthesis of acylglycerides with high nutritional value
title Valorization of glycerol through the enzymatic synthesis of acylglycerides with high nutritional value
spellingShingle Valorization of glycerol through the enzymatic synthesis of acylglycerides with high nutritional value
Sanchez, Daniel Alberto
ENZYMATIC ESTERIFICATION
FAT SUBSTITUTES
GLYCEROL VALORIZATION
NUTRITIONALLY VALUABLE ACYLGLYCERIDES
https://purl.org/becyt/ford/2.4
https://purl.org/becyt/ford/2
title_short Valorization of glycerol through the enzymatic synthesis of acylglycerides with high nutritional value
title_full Valorization of glycerol through the enzymatic synthesis of acylglycerides with high nutritional value
title_fullStr Valorization of glycerol through the enzymatic synthesis of acylglycerides with high nutritional value
title_full_unstemmed Valorization of glycerol through the enzymatic synthesis of acylglycerides with high nutritional value
title_sort Valorization of glycerol through the enzymatic synthesis of acylglycerides with high nutritional value
dc.creator.none.fl_str_mv Sanchez, Daniel Alberto
Tonetto, Gabriela Marta
Ferreira, María Luján
author Sanchez, Daniel Alberto
author_facet Sanchez, Daniel Alberto
Tonetto, Gabriela Marta
Ferreira, María Luján
author_role author
author2 Tonetto, Gabriela Marta
Ferreira, María Luján
author2_role author
author
dc.subject.none.fl_str_mv ENZYMATIC ESTERIFICATION
FAT SUBSTITUTES
GLYCEROL VALORIZATION
NUTRITIONALLY VALUABLE ACYLGLYCERIDES
https://purl.org/becyt/ford/2.4
https://purl.org/becyt/ford/2
topic ENZYMATIC ESTERIFICATION
FAT SUBSTITUTES
GLYCEROL VALORIZATION
NUTRITIONALLY VALUABLE ACYLGLYCERIDES
https://purl.org/becyt/ford/2.4
https://purl.org/becyt/ford/2
description The production of specific acylglycerides from the selective esterification of glycerol is an attractive alternative for the valorization of this by-product of the biodiesel industry. In this way, products with high added value are generated, increasing the profitability of the overall process and reducing an associated environmental threat. In this work, nutritional and medically interesting glycerides were obtained by enzymatic esterification through a two-stage process. In the first stage, 1,3-dicaprin was obtained by the regioselective esterification of glycerol and capric acid mediated by the commercial biocatalyst Lipozyme RM IM. Under optimal reaction conditions, 73% conversion of fatty acids and 76% selectivity to 1,3-dicaprin was achieved. A new model to explain the participation of lipase in the acyl migration reaction is presented. It evaluates the conditions in the microenvironment of the active site of the enzyme during the formation of the tetrahedral intermediate. In the second stage, the esterification of the sn-2 position of 1,3-dicaprin with palmitic acid was performed using the lipase from Burkholderia cepacia immobilized on chitosan as the biocatalyst. A biocatalyst containing 3 wt % of lipase showed good activity to esterify the sn-2 position of 1,3-dicaprin. A mixture of acylglycerides consisting mainly of capric acid esterified at sn-1 and sn-3, and of palmitic acid at the sn-2 position was obtained as the reaction product. The influence of the biocatalyst mass, the reaction temperature, and the molar ratio of substrates were evaluated for this reaction using a factorial design. Simple models were used to adjust the consumption of reagents and the generation of different products. The reaction product contained between 76% and 90% of acylglycerides with high nutritional value, depending on the reaction conditions.
publishDate 2020
dc.date.none.fl_str_mv 2020-01-14
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/126853
Sanchez, Daniel Alberto; Tonetto, Gabriela Marta; Ferreira, María Luján; Valorization of glycerol through the enzymatic synthesis of acylglycerides with high nutritional value; Molecular Diversity Preservation International; Catalysts; 10; 1; 14-1-2020; 1-24; 116
2073-4344
CONICET Digital
CONICET
url http://hdl.handle.net/11336/126853
identifier_str_mv Sanchez, Daniel Alberto; Tonetto, Gabriela Marta; Ferreira, María Luján; Valorization of glycerol through the enzymatic synthesis of acylglycerides with high nutritional value; Molecular Diversity Preservation International; Catalysts; 10; 1; 14-1-2020; 1-24; 116
2073-4344
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.3390/catal10010116
info:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/2073-4344/10/1/116
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Molecular Diversity Preservation International
publisher.none.fl_str_mv Molecular Diversity Preservation International
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
_version_ 1799195599901294592
spelling Valorization of glycerol through the enzymatic synthesis of acylglycerides with high nutritional valueSanchez, Daniel AlbertoTonetto, Gabriela MartaFerreira, María LujánENZYMATIC ESTERIFICATIONFAT SUBSTITUTESGLYCEROL VALORIZATIONNUTRITIONALLY VALUABLE ACYLGLYCERIDEShttps://purl.org/becyt/ford/2.4https://purl.org/becyt/ford/2The production of specific acylglycerides from the selective esterification of glycerol is an attractive alternative for the valorization of this by-product of the biodiesel industry. In this way, products with high added value are generated, increasing the profitability of the overall process and reducing an associated environmental threat. In this work, nutritional and medically interesting glycerides were obtained by enzymatic esterification through a two-stage process. In the first stage, 1,3-dicaprin was obtained by the regioselective esterification of glycerol and capric acid mediated by the commercial biocatalyst Lipozyme RM IM. Under optimal reaction conditions, 73% conversion of fatty acids and 76% selectivity to 1,3-dicaprin was achieved. A new model to explain the participation of lipase in the acyl migration reaction is presented. It evaluates the conditions in the microenvironment of the active site of the enzyme during the formation of the tetrahedral intermediate. In the second stage, the esterification of the sn-2 position of 1,3-dicaprin with palmitic acid was performed using the lipase from Burkholderia cepacia immobilized on chitosan as the biocatalyst. A biocatalyst containing 3 wt % of lipase showed good activity to esterify the sn-2 position of 1,3-dicaprin. A mixture of acylglycerides consisting mainly of capric acid esterified at sn-1 and sn-3, and of palmitic acid at the sn-2 position was obtained as the reaction product. The influence of the biocatalyst mass, the reaction temperature, and the molar ratio of substrates were evaluated for this reaction using a factorial design. Simple models were used to adjust the consumption of reagents and the generation of different products. The reaction product contained between 76% and 90% of acylglycerides with high nutritional value, depending on the reaction conditions.Fil: Sanchez, Daniel Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Planta Piloto de Ingeniería Química. Universidad Nacional del Sur. Planta Piloto de Ingeniería Química; Argentina. Universidad Nacional del Sur. Departamento de Ingeniería Química; ArgentinaFil: Tonetto, Gabriela Marta. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Planta Piloto de Ingeniería Química. Universidad Nacional del Sur. Planta Piloto de Ingeniería Química; Argentina. Universidad Nacional del Sur. Departamento de Ingeniería Química; ArgentinaFil: Ferreira, María Luján. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Planta Piloto de Ingeniería Química. Universidad Nacional del Sur. Planta Piloto de Ingeniería Química; Argentina. Universidad Nacional del Sur. Departamento de Química; ArgentinaMolecular Diversity Preservation International2020-01-14info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/126853Sanchez, Daniel Alberto; Tonetto, Gabriela Marta; Ferreira, María Luján; Valorization of glycerol through the enzymatic synthesis of acylglycerides with high nutritional value; Molecular Diversity Preservation International; Catalysts; 10; 1; 14-1-2020; 1-24; 1162073-4344CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.3390/catal10010116info:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/2073-4344/10/1/116info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2024-05-08T13:57:38Zoai:ri.conicet.gov.ar:11336/126853instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982024-05-08 13:57:38.519CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
score 15.811543

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