Transglycosylation specificity of Acremonium sp. α-rhamnosyl-β-glucosidase and its application to the synthesis of the new fluorogenic substrate 4-methylumbelliferyl-rutinoside

Autores
Mazzaferro, Laura; Piñuel, Maria Lucrecia; Erra Balsells, Rosa; Giudicessi, Silvana Laura; Breccia, Javier Dario
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Transglycosylation potential of the fungal diglycosidase α-rhamnosyl-β-glucosidase was explored. The biocatalyst was shown to have broad acceptor specificity toward aliphatic and aromatic alcohols. This feature allowed the synthesis of the diglycoconjugated fluorogenic substrate 4-methylumbelliferyl-rutinoside. The synthesis was performed in one step from the corresponding aglycone, 4-methylumbelliferone, and hesperidin as rutinose donor. 4-Methylumbelliferyl-rutinoside was produced in an agitated reactor using the immobilized biocatalyst with a 16% yield regarding the sugar acceptor. The compound was purified by solvent extraction and silica gel chromatography. MALDI-TOF/TOF data recorded for the [M+Na]+ ions correlated with the theoretical monoisotopic mass (calcd [M+Na]+: 507.44 m/z; obs. [M+Na]+: 507.465 m/z). 4-Methylumbelliferyl-rutinoside differs from 4-methylumbelliferyl-glucoside in the rhamnosyl substitution at the C-6 of glucose, and this property brings about the possibility to explore in nature the occurrence of endo-β-glucosidases by zymographic analysis.
Fil: Mazzaferro, Laura. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Instituto de Ciencias de la Tierra y Ambientales de la Pampa; Argentina. Universidad Nacional de la Pampa. Facultad de Ciencias Exactas y Naturales. Departamento de Quimica; Argentina
Fil: Piñuel, Maria Lucrecia. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Instituto de Ciencias de la Tierra y Ambientales de la Pampa; Argentina. Universidad Nacional de la Pampa. Facultad de Ciencias Exactas y Naturales. Departamento de Quimica; Argentina
Fil: Erra Balsells, Rosa. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Giudicessi, Silvana Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones En Hidratos de Carbono; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Breccia, Javier Dario. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Instituto de Ciencias de la Tierra y Ambientales de la Pampa; Argentina. Universidad Nacional de la Pampa. Facultad de Ciencias Exactas y Naturales. Departamento de Quimica; Argentina
Materia
Diglycosidase
Hesperidin
Zymogram
Acremonium Sp. Dsm 24697
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/14115
Acceder
id CONICETDig_9900d25311b7bea038b82687de690905
oai_identifier_str oai:ri.conicet.gov.ar:11336/14115
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Transglycosylation specificity of Acremonium sp. α-rhamnosyl-β-glucosidase and its application to the synthesis of the new fluorogenic substrate 4-methylumbelliferyl-rutinosideMazzaferro, LauraPiñuel, Maria LucreciaErra Balsells, RosaGiudicessi, Silvana LauraBreccia, Javier DarioDiglycosidaseHesperidinZymogramAcremonium Sp. Dsm 24697https://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Transglycosylation potential of the fungal diglycosidase α-rhamnosyl-β-glucosidase was explored. The biocatalyst was shown to have broad acceptor specificity toward aliphatic and aromatic alcohols. This feature allowed the synthesis of the diglycoconjugated fluorogenic substrate 4-methylumbelliferyl-rutinoside. The synthesis was performed in one step from the corresponding aglycone, 4-methylumbelliferone, and hesperidin as rutinose donor. 4-Methylumbelliferyl-rutinoside was produced in an agitated reactor using the immobilized biocatalyst with a 16% yield regarding the sugar acceptor. The compound was purified by solvent extraction and silica gel chromatography. MALDI-TOF/TOF data recorded for the [M+Na]+ ions correlated with the theoretical monoisotopic mass (calcd [M+Na]+: 507.44 m/z; obs. [M+Na]+: 507.465 m/z). 4-Methylumbelliferyl-rutinoside differs from 4-methylumbelliferyl-glucoside in the rhamnosyl substitution at the C-6 of glucose, and this property brings about the possibility to explore in nature the occurrence of endo-β-glucosidases by zymographic analysis.Fil: Mazzaferro, Laura. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Instituto de Ciencias de la Tierra y Ambientales de la Pampa; Argentina. Universidad Nacional de la Pampa. Facultad de Ciencias Exactas y Naturales. Departamento de Quimica; ArgentinaFil: Piñuel, Maria Lucrecia. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Instituto de Ciencias de la Tierra y Ambientales de la Pampa; Argentina. Universidad Nacional de la Pampa. Facultad de Ciencias Exactas y Naturales. Departamento de Quimica; ArgentinaFil: Erra Balsells, Rosa. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; ArgentinaFil: Giudicessi, Silvana Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones En Hidratos de Carbono; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; ArgentinaFil: Breccia, Javier Dario. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Instituto de Ciencias de la Tierra y Ambientales de la Pampa; Argentina. Universidad Nacional de la Pampa. Facultad de Ciencias Exactas y Naturales. Departamento de Quimica; ArgentinaElsevier2012-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/14115Mazzaferro, Laura; Piñuel, Maria Lucrecia; Erra Balsells, Rosa; Giudicessi, Silvana Laura; Breccia, Javier Dario; Transglycosylation specificity of Acremonium sp. α-rhamnosyl-β-glucosidase and its application to the synthesis of the new fluorogenic substrate 4-methylumbelliferyl-rutinoside; Elsevier; Carbohydrate Research; 347; 1; 1-2012; 69-750008-6215enginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.carres.2011.11.008info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0008621511005556info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:22:11Zoai:ri.conicet.gov.ar:11336/14115instacron: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:34982025-10-15 14:22:11.787CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Transglycosylation specificity of Acremonium sp. α-rhamnosyl-β-glucosidase and its application to the synthesis of the new fluorogenic substrate 4-methylumbelliferyl-rutinoside
title Transglycosylation specificity of Acremonium sp. α-rhamnosyl-β-glucosidase and its application to the synthesis of the new fluorogenic substrate 4-methylumbelliferyl-rutinoside
spellingShingle Transglycosylation specificity of Acremonium sp. α-rhamnosyl-β-glucosidase and its application to the synthesis of the new fluorogenic substrate 4-methylumbelliferyl-rutinoside
Mazzaferro, Laura
Diglycosidase
Hesperidin
Zymogram
Acremonium Sp. Dsm 24697
title_short Transglycosylation specificity of Acremonium sp. α-rhamnosyl-β-glucosidase and its application to the synthesis of the new fluorogenic substrate 4-methylumbelliferyl-rutinoside
title_full Transglycosylation specificity of Acremonium sp. α-rhamnosyl-β-glucosidase and its application to the synthesis of the new fluorogenic substrate 4-methylumbelliferyl-rutinoside
title_fullStr Transglycosylation specificity of Acremonium sp. α-rhamnosyl-β-glucosidase and its application to the synthesis of the new fluorogenic substrate 4-methylumbelliferyl-rutinoside
title_full_unstemmed Transglycosylation specificity of Acremonium sp. α-rhamnosyl-β-glucosidase and its application to the synthesis of the new fluorogenic substrate 4-methylumbelliferyl-rutinoside
title_sort Transglycosylation specificity of Acremonium sp. α-rhamnosyl-β-glucosidase and its application to the synthesis of the new fluorogenic substrate 4-methylumbelliferyl-rutinoside
dc.creator.none.fl_str_mv Mazzaferro, Laura
Piñuel, Maria Lucrecia
Erra Balsells, Rosa
Giudicessi, Silvana Laura
Breccia, Javier Dario
author Mazzaferro, Laura
author_facet Mazzaferro, Laura
Piñuel, Maria Lucrecia
Erra Balsells, Rosa
Giudicessi, Silvana Laura
Breccia, Javier Dario
author_role author
author2 Piñuel, Maria Lucrecia
Erra Balsells, Rosa
Giudicessi, Silvana Laura
Breccia, Javier Dario
author2_role author
author
author
author
dc.subject.none.fl_str_mv Diglycosidase
Hesperidin
Zymogram
Acremonium Sp. Dsm 24697
topic Diglycosidase
Hesperidin
Zymogram
Acremonium Sp. Dsm 24697
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Transglycosylation potential of the fungal diglycosidase α-rhamnosyl-β-glucosidase was explored. The biocatalyst was shown to have broad acceptor specificity toward aliphatic and aromatic alcohols. This feature allowed the synthesis of the diglycoconjugated fluorogenic substrate 4-methylumbelliferyl-rutinoside. The synthesis was performed in one step from the corresponding aglycone, 4-methylumbelliferone, and hesperidin as rutinose donor. 4-Methylumbelliferyl-rutinoside was produced in an agitated reactor using the immobilized biocatalyst with a 16% yield regarding the sugar acceptor. The compound was purified by solvent extraction and silica gel chromatography. MALDI-TOF/TOF data recorded for the [M+Na]+ ions correlated with the theoretical monoisotopic mass (calcd [M+Na]+: 507.44 m/z; obs. [M+Na]+: 507.465 m/z). 4-Methylumbelliferyl-rutinoside differs from 4-methylumbelliferyl-glucoside in the rhamnosyl substitution at the C-6 of glucose, and this property brings about the possibility to explore in nature the occurrence of endo-β-glucosidases by zymographic analysis.
Fil: Mazzaferro, Laura. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Instituto de Ciencias de la Tierra y Ambientales de la Pampa; Argentina. Universidad Nacional de la Pampa. Facultad de Ciencias Exactas y Naturales. Departamento de Quimica; Argentina
Fil: Piñuel, Maria Lucrecia. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Instituto de Ciencias de la Tierra y Ambientales de la Pampa; Argentina. Universidad Nacional de la Pampa. Facultad de Ciencias Exactas y Naturales. Departamento de Quimica; Argentina
Fil: Erra Balsells, Rosa. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Giudicessi, Silvana Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones En Hidratos de Carbono; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Breccia, Javier Dario. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Instituto de Ciencias de la Tierra y Ambientales de la Pampa; Argentina. Universidad Nacional de la Pampa. Facultad de Ciencias Exactas y Naturales. Departamento de Quimica; Argentina
description Transglycosylation potential of the fungal diglycosidase α-rhamnosyl-β-glucosidase was explored. The biocatalyst was shown to have broad acceptor specificity toward aliphatic and aromatic alcohols. This feature allowed the synthesis of the diglycoconjugated fluorogenic substrate 4-methylumbelliferyl-rutinoside. The synthesis was performed in one step from the corresponding aglycone, 4-methylumbelliferone, and hesperidin as rutinose donor. 4-Methylumbelliferyl-rutinoside was produced in an agitated reactor using the immobilized biocatalyst with a 16% yield regarding the sugar acceptor. The compound was purified by solvent extraction and silica gel chromatography. MALDI-TOF/TOF data recorded for the [M+Na]+ ions correlated with the theoretical monoisotopic mass (calcd [M+Na]+: 507.44 m/z; obs. [M+Na]+: 507.465 m/z). 4-Methylumbelliferyl-rutinoside differs from 4-methylumbelliferyl-glucoside in the rhamnosyl substitution at the C-6 of glucose, and this property brings about the possibility to explore in nature the occurrence of endo-β-glucosidases by zymographic analysis.
publishDate 2012
dc.date.none.fl_str_mv 2012-01
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/11336/14115
Mazzaferro, Laura; Piñuel, Maria Lucrecia; Erra Balsells, Rosa; Giudicessi, Silvana Laura; Breccia, Javier Dario; Transglycosylation specificity of Acremonium sp. α-rhamnosyl-β-glucosidase and its application to the synthesis of the new fluorogenic substrate 4-methylumbelliferyl-rutinoside; Elsevier; Carbohydrate Research; 347; 1; 1-2012; 69-75
0008-6215
url http://hdl.handle.net/11336/14115
identifier_str_mv Mazzaferro, Laura; Piñuel, Maria Lucrecia; Erra Balsells, Rosa; Giudicessi, Silvana Laura; Breccia, Javier Dario; Transglycosylation specificity of Acremonium sp. α-rhamnosyl-β-glucosidase and its application to the synthesis of the new fluorogenic substrate 4-methylumbelliferyl-rutinoside; Elsevier; Carbohydrate Research; 347; 1; 1-2012; 69-75
0008-6215
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.carres.2011.11.008
info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0008621511005556
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
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_ 1846082618603339776
score 13.22299

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