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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/14115
Ver los metadatos del registro completo
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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 Técnicas2025-09-29T09:34:00Zoai: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:34982025-09-29 09:34:00.551CONICET 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 |
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1844613049529401344 |
score |
13.070432 |