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dc.contributor.author
Mazzaferro, Laura
dc.contributor.author
Weiz, Gisela
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Braun, Lucas Ezequiel
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Kotik, Michael
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Pelantová, Helena
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Kren, Vladimír
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Breccia, Javier Dario
dc.date.available
2020-08-25T20:28:16Z
dc.date.issued
2019-01
dc.identifier.citation
Mazzaferro, Laura; Weiz, Gisela; Braun, Lucas Ezequiel; Kotik, Michael; Pelantová, Helena; et al.; Enzyme-mediated transglycosylation of rutinose (6-O-α-L-rhamnosyl-D-glucose) to phenolic compounds by a diglycosidase from Acremonium sp. DSM 24697; Portland Press; Biotechnology and Applied Biochemistry; 66; 1; 1-2019; 53-59
dc.identifier.issn
0885-4513
dc.identifier.uri
http://hdl.handle.net/11336/112405
dc.description.abstract
The structure of the carbohydrate moiety of a natural phenolic glycoside can have a significant effect on the molecular interactions and physicochemical and pharmacokinetic properties of the entire compound, which may include anti-inflammatory and anticancer activities. The enzyme 6-O-α-rhamnosyl-β-glucosidase (EC 3.2.1.168) has the capacity to transfer the rutinosyl moiety (6-O-α-L-rhamnopyranosylβ-D-glucopyranose) from 7-O-rutinosylated flavonoids to hydroxylated organic compounds. This transglycosylation reaction was optimized using hydroquinone (HQ) and hesperidin as rutinose acceptor and donor, respectively. Since HQ undergoes oxidation in a neutral to alkaline aqueous environment, the transglycosylation process was carried out at pH values 6.0. The structure of 4-hydroxyphenyl-β-rutinoside was confirmed by NMR, that is, a single glycosylated product with a free hydroxyl group was formed. The highest yield of 4-hydroxyphenyl-β-rutinoside (38%, regarding hesperidin) was achieved in a 2-h process at pH 5.0 and 30 ◦C, with 36 mM OH-acceptor and 5% (v/v) cosolvent. Under the same conditions, the enzyme synthesized glycoconjugates of various phenolic compounds (phloroglucinol, resorcinol, pyrogallol, catechol), with yields between 12% and 28% and an apparent direct linear relationship between the yield and the pKa value of the aglycon. This work is a contribution to the development of convenient and sustainable processes for the glycosylation of small phenolic compounds.
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application/pdf
dc.language.iso
eng
dc.publisher
Portland Press
dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
HESPERIDIN
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HYDROQUINONE
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Α-RHAMNOSYL-Β-GLUCOSIDASE
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Bioprocesamiento Tecnológico, Biocatálisis, Fermentación
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Biotecnología Industrial
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INGENIERÍAS Y TECNOLOGÍAS
dc.title
Enzyme-mediated transglycosylation of rutinose (6-O-α-L-rhamnosyl-D-glucose) to phenolic compounds by a diglycosidase from Acremonium sp. DSM 24697
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2020-05-04T20:53:45Z
dc.journal.volume
66
dc.journal.number
1
dc.journal.pagination
53-59
dc.journal.pais
Reino Unido
dc.journal.ciudad
Londres
dc.description.fil
Fil: Mazzaferro, Laura. Universidad Nacional de La Pampa; Argentina. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Centro Cientifico Tecnologico Conicet - Patagonia Confluencia. Instituto de Ciencias de la Tierra y Ambientales de la Pampa. Grupo Vinculado Fundacion Centro de Salud E Investigaciones Medicas | Universidad Nacional de la Pampa. Facultad de Ciencias Exactas y Naturales. Instituto de Ciencias de la Tierra y Ambientales de la Pampa. Grupo Vinculado Fundacion Centro de Salud E Investigaciones Medicas.; Argentina
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Fil: Weiz, Gisela. Universidad Nacional de La Pampa; Argentina. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Centro Cientifico Tecnologico Conicet - Patagonia Confluencia. Instituto de Ciencias de la Tierra y Ambientales de la Pampa. Grupo Vinculado Fundacion Centro de Salud E Investigaciones Medicas | Universidad Nacional de la Pampa. Facultad de Ciencias Exactas y Naturales. Instituto de Ciencias de la Tierra y Ambientales de la Pampa. Grupo Vinculado Fundacion Centro de Salud E Investigaciones Medicas.; Argentina
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Fil: Braun, Lucas Ezequiel. Universidad Nacional de La Pampa; Argentina. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Centro Cientifico Tecnologico Conicet - Patagonia Confluencia. Instituto de Ciencias de la Tierra y Ambientales de la Pampa. Grupo Vinculado Fundacion Centro de Salud E Investigaciones Medicas | Universidad Nacional de la Pampa. Facultad de Ciencias Exactas y Naturales. Instituto de Ciencias de la Tierra y Ambientales de la Pampa. Grupo Vinculado Fundacion Centro de Salud E Investigaciones Medicas.; Argentina
dc.description.fil
Fil: Kotik, Michael. Czech Academy of Sciences. Institute of Organic Chemistry and Biochemistry; República Checa
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Fil: Pelantová, Helena. Czech Academy of Sciences. Institute of Organic Chemistry and Biochemistry; República Checa
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Fil: Kren, Vladimír. Czech Academy of Sciences. Institute of Organic Chemistry and Biochemistry; República Checa
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Fil: Breccia, Javier Dario. Universidad Nacional de La Pampa; Argentina. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Centro Cientifico Tecnologico Conicet - Patagonia Confluencia. Instituto de Ciencias de la Tierra y Ambientales de la Pampa. Grupo Vinculado Fundacion Centro de Salud E Investigaciones Medicas | Universidad Nacional de la Pampa. Facultad de Ciencias Exactas y Naturales. Instituto de Ciencias de la Tierra y Ambientales de la Pampa. Grupo Vinculado Fundacion Centro de Salud E Investigaciones Medicas.; Argentina
dc.journal.title
Biotechnology and Applied Biochemistry
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/https://iubmb.onlinelibrary.wiley.com/doi/abs/10.1002/bab.1695
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1002/bab.1695
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