Synthesis of sn-2 docosahexaenoyl monoacylglycerol by mild enzymatic transesterification of docosahexaenoic acid ethyl ester and glycerol in a solvent-free system

The enzymatic transesterification of docosahexaenoic acid (DHA) ethyl ester with glycerol was performed with several lipases in a solvent-free system and it involves the initial formation of sn-2 docosahexaenyl monoacylglyceride. This DHA derivative is highly relevant for improving the bioavailabili...

ver descrição completa

Detalhes bibliográficos
Autores: Moreno-Pérez, Sonia, Luna, Pilar, Señoráns, Francisco J., Guisán, José Manuel, Fernández-Lorente, Gloria
Formato: artículo
Estado:Versión publicada
Fecha de publicación:2016
País:España
Recursos:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/157418
Acesso em linha:http://hdl.handle.net/10261/157418
Access Level:acceso abierto
Palavra-chave:Immobilized lipases in solvent-free systems
Sn-2 regioselective transesterification of DHA-EE with glycerol
Novel DHA derivatives
id ES_137972cfa053fcd375d3f5fccafae0f8
oai_identifier_str oai:digital.csic.es:10261/157418
network_acronym_str ES
network_name_str España
repository_id_str
spelling Synthesis of sn-2 docosahexaenoyl monoacylglycerol by mild enzymatic transesterification of docosahexaenoic acid ethyl ester and glycerol in a solvent-free systemMoreno-Pérez, SoniaLuna, PilarSeñoráns, Francisco J.Guisán, José ManuelFernández-Lorente, GloriaImmobilized lipases in solvent-free systemsSn-2 regioselective transesterification of DHA-EE with glycerolNovel DHA derivativesThe enzymatic transesterification of docosahexaenoic acid (DHA) ethyl ester with glycerol was performed with several lipases in a solvent-free system and it involves the initial formation of sn-2 docosahexaenyl monoacylglyceride. This DHA derivative is highly relevant for improving the bioavailability of DHA and it has received increasing interest in the field of nutrition. Three commercial lipases, from Rhizomucor miehei (RML), Alcaligenes sp (QL), and Candida antarctica-fraction B (CALB) were tested. In certain cases (CALB), using an excess of DHA ethyl ester and high temperatures the transesterification reaction continues to the formation of triacylglycerides, but in other cases, sn-2 monoacylglyceride (2-MG) is the unique synthetic product even in the presence of high concentrations of DHA ethyl ester. At low temperatures (e.g. 37°C), RML derivatives synthesize only 2-MG in 15 min. These very mild conditions are very interesting for the thermal oxidative stability of the omega-3 fatty acid and for the thermal stability of the biocatalyst. Using Normal Phase HPLC-ELSD and accurate markers, the formation of the 2-MG was confirmed.This work was sponsored by the Spanish Ministry of Science and Innovation 223 [project number AGL-2009-07526], [project number BIO2012-36861].Peer reviewedCogent OAMinisterio de Ciencia e Innovación (España)Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]201720172016info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Publisher's versioninfo:eu-repo/semantics/publishedVersionhttp://hdl.handle.net/10261/157418reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Ingléshttps://www.doi.org/10.1080/23311932.2016.1164569Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/1574182026-05-22T06:33:51Z
dc.title.none.fl_str_mv Synthesis of sn-2 docosahexaenoyl monoacylglycerol by mild enzymatic transesterification of docosahexaenoic acid ethyl ester and glycerol in a solvent-free system
title Synthesis of sn-2 docosahexaenoyl monoacylglycerol by mild enzymatic transesterification of docosahexaenoic acid ethyl ester and glycerol in a solvent-free system
spellingShingle Synthesis of sn-2 docosahexaenoyl monoacylglycerol by mild enzymatic transesterification of docosahexaenoic acid ethyl ester and glycerol in a solvent-free system
Moreno-Pérez, Sonia
Immobilized lipases in solvent-free systems
Sn-2 regioselective transesterification of DHA-EE with glycerol
Novel DHA derivatives
title_short Synthesis of sn-2 docosahexaenoyl monoacylglycerol by mild enzymatic transesterification of docosahexaenoic acid ethyl ester and glycerol in a solvent-free system
title_full Synthesis of sn-2 docosahexaenoyl monoacylglycerol by mild enzymatic transesterification of docosahexaenoic acid ethyl ester and glycerol in a solvent-free system
title_fullStr Synthesis of sn-2 docosahexaenoyl monoacylglycerol by mild enzymatic transesterification of docosahexaenoic acid ethyl ester and glycerol in a solvent-free system
title_full_unstemmed Synthesis of sn-2 docosahexaenoyl monoacylglycerol by mild enzymatic transesterification of docosahexaenoic acid ethyl ester and glycerol in a solvent-free system
title_sort Synthesis of sn-2 docosahexaenoyl monoacylglycerol by mild enzymatic transesterification of docosahexaenoic acid ethyl ester and glycerol in a solvent-free system
dc.creator.none.fl_str_mv Moreno-Pérez, Sonia
Luna, Pilar
Señoráns, Francisco J.
Guisán, José Manuel
Fernández-Lorente, Gloria
author Moreno-Pérez, Sonia
author_facet Moreno-Pérez, Sonia
Luna, Pilar
Señoráns, Francisco J.
Guisán, José Manuel
Fernández-Lorente, Gloria
author_role author
author2 Luna, Pilar
Señoráns, Francisco J.
Guisán, José Manuel
Fernández-Lorente, Gloria
author2_role author
author
author
author
dc.contributor.none.fl_str_mv Ministerio de Ciencia e Innovación (España)
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Immobilized lipases in solvent-free systems
Sn-2 regioselective transesterification of DHA-EE with glycerol
Novel DHA derivatives
topic Immobilized lipases in solvent-free systems
Sn-2 regioselective transesterification of DHA-EE with glycerol
Novel DHA derivatives
description The enzymatic transesterification of docosahexaenoic acid (DHA) ethyl ester with glycerol was performed with several lipases in a solvent-free system and it involves the initial formation of sn-2 docosahexaenyl monoacylglyceride. This DHA derivative is highly relevant for improving the bioavailability of DHA and it has received increasing interest in the field of nutrition. Three commercial lipases, from Rhizomucor miehei (RML), Alcaligenes sp (QL), and Candida antarctica-fraction B (CALB) were tested. In certain cases (CALB), using an excess of DHA ethyl ester and high temperatures the transesterification reaction continues to the formation of triacylglycerides, but in other cases, sn-2 monoacylglyceride (2-MG) is the unique synthetic product even in the presence of high concentrations of DHA ethyl ester. At low temperatures (e.g. 37°C), RML derivatives synthesize only 2-MG in 15 min. These very mild conditions are very interesting for the thermal oxidative stability of the omega-3 fatty acid and for the thermal stability of the biocatalyst. Using Normal Phase HPLC-ELSD and accurate markers, the formation of the 2-MG was confirmed.
publishDate 2016
dc.date.none.fl_str_mv 2016
2017
2017
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Publisher's version
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/157418
url http://hdl.handle.net/10261/157418
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv https://www.doi.org/10.1080/23311932.2016.1164569
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Cogent OA
publisher.none.fl_str_mv Cogent OA
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
_version_ 1869403678568349696
score 15,811543

Registos relacionados