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
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/2107
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling 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 Técnicas2025-10-22T11:06:57Zoai: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:34982025-10-22 11:06:58.183CONICET 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_ 1846781377710653440
score 12.928904

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