Synthesis of the (1→6)-linked thiodisaccharide of galactofuranose. Inhibitory activity against a β-galactofuranosidase
- Autores
- Repetto, Evangelina; Marino, María Carla; Varela, Oscar Jose
- Año de publicación
- 2013
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- Methyl (methyl alpha,beta-D-galactofuranosid)uronate was employed as the starting compound,which was per-O-silylated with TBSCl and reduced with LiAlH4 to afford methyl 2,3,5-tri-O-tert-butyldimethylsilyl-b-D-galactofuranoside (2b) as akey precursor for the preparation of methyl per-O-tert-butyldimethylsilyl-6-thio-b-D-galactofuranos ide (12). The free thiol group of 12 was glycosylated and the product O-deprotected to afford the target b-D-Galf-S-(1,6)-b-D-Galf-OMe (14). The conformations of this thiodisaccharide were preliminarily studied using combined theoretical calculatio ns and NMR data.Further-more, the glycomimetic 14 showed to be a competitiv einhibitor of the beta-galactofuranosidase from Penicillum fellutanum (Ki = 3.62 mM).
Fil: Repetto, Evangelina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Marino, María Carla. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Varela, Oscar Jose. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina - Materia
-
Galactofuranoside Precursors
Thiogalactofuranosyl Disaccharide
6-Thiogalactofuranose
Conformational Analysis
Exo B-D-Galactofuranosidase
Enzyme Inhibition - 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:11336/2107
Ver los metadatos del registro completo
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Synthesis of the (1→6)-linked thiodisaccharide of galactofuranose. Inhibitory activity against a β-galactofuranosidaseRepetto, EvangelinaMarino, María CarlaVarela, Oscar JoseGalactofuranoside PrecursorsThiogalactofuranosyl Disaccharide6-ThiogalactofuranoseConformational AnalysisExo B-D-GalactofuranosidaseEnzyme Inhibitionhttps://purl.org/becyt/ford/1.6https://purl.org/becyt/ford/1Methyl (methyl alpha,beta-D-galactofuranosid)uronate was employed as the starting compound,which was per-O-silylated with TBSCl and reduced with LiAlH4 to afford methyl 2,3,5-tri-O-tert-butyldimethylsilyl-b-D-galactofuranoside (2b) as akey precursor for the preparation of methyl per-O-tert-butyldimethylsilyl-6-thio-b-D-galactofuranos ide (12). The free thiol group of 12 was glycosylated and the product O-deprotected to afford the target b-D-Galf-S-(1,6)-b-D-Galf-OMe (14). The conformations of this thiodisaccharide were preliminarily studied using combined theoretical calculatio ns and NMR data.Further-more, the glycomimetic 14 showed to be a competitiv einhibitor of the beta-galactofuranosidase from Penicillum fellutanum (Ki = 3.62 mM).Fil: Repetto, Evangelina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; ArgentinaFil: Marino, María Carla. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; ArgentinaFil: Varela, Oscar Jose. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; ArgentinaElsevier2013-06-01info: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/11336/2107Repetto, Evangelina; Marino, María Carla; Varela, Oscar Jose; Synthesis of the (1→6)-linked thiodisaccharide of galactofuranose. Inhibitory activity against a β-galactofuranosidase; Elsevier; Bioorganic & Medicinal Chemistry; 21; 11; 1-6-2013; 3327-33330968-0896enginfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0968089613002551info:eu-repo/semantics/altIdentifier/doi/10.1016/j.bmc.2013.02.057info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:38:40Zoai:ri.conicet.gov.ar:11336/2107instacron: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 09:38:41.15CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
dc.title.none.fl_str_mv |
Synthesis of the (1→6)-linked thiodisaccharide of galactofuranose. Inhibitory activity against a β-galactofuranosidase |
title |
Synthesis of the (1→6)-linked thiodisaccharide of galactofuranose. Inhibitory activity against a β-galactofuranosidase |
spellingShingle |
Synthesis of the (1→6)-linked thiodisaccharide of galactofuranose. Inhibitory activity against a β-galactofuranosidase Repetto, Evangelina Galactofuranoside Precursors Thiogalactofuranosyl Disaccharide 6-Thiogalactofuranose Conformational Analysis Exo B-D-Galactofuranosidase Enzyme Inhibition |
title_short |
Synthesis of the (1→6)-linked thiodisaccharide of galactofuranose. Inhibitory activity against a β-galactofuranosidase |
title_full |
Synthesis of the (1→6)-linked thiodisaccharide of galactofuranose. Inhibitory activity against a β-galactofuranosidase |
title_fullStr |
Synthesis of the (1→6)-linked thiodisaccharide of galactofuranose. Inhibitory activity against a β-galactofuranosidase |
title_full_unstemmed |
Synthesis of the (1→6)-linked thiodisaccharide of galactofuranose. Inhibitory activity against a β-galactofuranosidase |
title_sort |
Synthesis of the (1→6)-linked thiodisaccharide of galactofuranose. Inhibitory activity against a β-galactofuranosidase |
dc.creator.none.fl_str_mv |
Repetto, Evangelina Marino, María Carla Varela, Oscar Jose |
author |
Repetto, Evangelina |
author_facet |
Repetto, Evangelina Marino, María Carla Varela, Oscar Jose |
author_role |
author |
author2 |
Marino, María Carla Varela, Oscar Jose |
author2_role |
author author |
dc.subject.none.fl_str_mv |
Galactofuranoside Precursors Thiogalactofuranosyl Disaccharide 6-Thiogalactofuranose Conformational Analysis Exo B-D-Galactofuranosidase Enzyme Inhibition |
topic |
Galactofuranoside Precursors Thiogalactofuranosyl Disaccharide 6-Thiogalactofuranose Conformational Analysis Exo B-D-Galactofuranosidase Enzyme Inhibition |
purl_subject.fl_str_mv |
https://purl.org/becyt/ford/1.6 https://purl.org/becyt/ford/1 |
dc.description.none.fl_txt_mv |
Methyl (methyl alpha,beta-D-galactofuranosid)uronate was employed as the starting compound,which was per-O-silylated with TBSCl and reduced with LiAlH4 to afford methyl 2,3,5-tri-O-tert-butyldimethylsilyl-b-D-galactofuranoside (2b) as akey precursor for the preparation of methyl per-O-tert-butyldimethylsilyl-6-thio-b-D-galactofuranos ide (12). The free thiol group of 12 was glycosylated and the product O-deprotected to afford the target b-D-Galf-S-(1,6)-b-D-Galf-OMe (14). The conformations of this thiodisaccharide were preliminarily studied using combined theoretical calculatio ns and NMR data.Further-more, the glycomimetic 14 showed to be a competitiv einhibitor of the beta-galactofuranosidase from Penicillum fellutanum (Ki = 3.62 mM). Fil: Repetto, Evangelina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina Fil: Marino, María Carla. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina Fil: Varela, Oscar Jose. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina |
description |
Methyl (methyl alpha,beta-D-galactofuranosid)uronate was employed as the starting compound,which was per-O-silylated with TBSCl and reduced with LiAlH4 to afford methyl 2,3,5-tri-O-tert-butyldimethylsilyl-b-D-galactofuranoside (2b) as akey precursor for the preparation of methyl per-O-tert-butyldimethylsilyl-6-thio-b-D-galactofuranos ide (12). The free thiol group of 12 was glycosylated and the product O-deprotected to afford the target b-D-Galf-S-(1,6)-b-D-Galf-OMe (14). The conformations of this thiodisaccharide were preliminarily studied using combined theoretical calculatio ns and NMR data.Further-more, the glycomimetic 14 showed to be a competitiv einhibitor of the beta-galactofuranosidase from Penicillum fellutanum (Ki = 3.62 mM). |
publishDate |
2013 |
dc.date.none.fl_str_mv |
2013-06-01 |
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/11336/2107 Repetto, Evangelina; Marino, María Carla; Varela, Oscar Jose; Synthesis of the (1→6)-linked thiodisaccharide of galactofuranose. Inhibitory activity against a β-galactofuranosidase; Elsevier; Bioorganic & Medicinal Chemistry; 21; 11; 1-6-2013; 3327-3333 0968-0896 |
url |
http://hdl.handle.net/11336/2107 |
identifier_str_mv |
Repetto, Evangelina; Marino, María Carla; Varela, Oscar Jose; Synthesis of the (1→6)-linked thiodisaccharide of galactofuranose. Inhibitory activity against a β-galactofuranosidase; Elsevier; Bioorganic & Medicinal Chemistry; 21; 11; 1-6-2013; 3327-3333 0968-0896 |
dc.language.none.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0968089613002551 info:eu-repo/semantics/altIdentifier/doi/10.1016/j.bmc.2013.02.057 |
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_ |
1844613222810779648 |
score |
13.070432 |