Synthesis of the (1→6)-linked thiodisaccharide of galactofuranose: Inhibitory activity against a β-galactofuranosidase

A new (1→6)-linked thiodisaccharide formed by two galactofuranosyl units has been synthesized. Methyl (methyl α,β-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-β-d-...

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Publicado:	2013
Materias:	β-d-Galactofuranosidase 6-Thiogalactofuranose Conformational analysis exo Enzyme inhibition Thiogalactofuranosyl disaccharide carbohydrate derivative disaccharide galactofuranose galactofuranosidase glycosidase methyl 6 (beta dextro galactofuranosyl) 6 thio beta dextro galactofuranoside unclassified drug article drug conformation drug synthesis enzyme inhibition mathematical analysis nuclear magnetic resonance spectroscopy Penicillium Penicillum fellutanum Antifungal Agents Carbohydrate Conformation Disaccharides Fungal Proteins Galactose Glycoside Hydrolases Glycosylation Kinetics Magnetic Resonance Spectroscopy Thiogalactosides
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v21_n11_p3327_Repetto http://hdl.handle.net/20.500.12110/paper_09680896_v21_n11_p3327_Repetto
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

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spelling	paper:paper_09680896_v21_n11_p3327_Repetto2023-06-08T15:58:56Z Synthesis of the (1→6)-linked thiodisaccharide of galactofuranose: Inhibitory activity against a β-galactofuranosidase β-d-Galactofuranosidase 6-Thiogalactofuranose Conformational analysis exo Enzyme inhibition Thiogalactofuranosyl disaccharide carbohydrate derivative disaccharide galactofuranose galactofuranosidase glycosidase methyl 6 (beta dextro galactofuranosyl) 6 thio beta dextro galactofuranoside unclassified drug article drug conformation drug synthesis enzyme inhibition mathematical analysis nuclear magnetic resonance spectroscopy Penicillium Penicillum fellutanum Antifungal Agents Carbohydrate Conformation Disaccharides Fungal Proteins Galactose Glycoside Hydrolases Glycosylation Kinetics Magnetic Resonance Spectroscopy Penicillium Thiogalactosides A new (1→6)-linked thiodisaccharide formed by two galactofuranosyl units has been synthesized. Methyl (methyl α,β-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-β-d-galactofuranoside (2β) as a key precursor for the preparation of methyl per-O-tert-butyldimethylsilyl-6-thio-β-d- galactofuranoside (12). The free thiol group of 12 was glycosylated and the product O-deprotected to afford the target β-d-Galf-S-(1→6)-β-d- Galf-OMe (14). The conformations of this thiodisaccharide were preliminarily studied using combined theoretical calculations and NMR data. Furthermore, the glycomimetic 14 showed to be a competitive inhibitor of the β- galactofuranosidase from Penicillum fellutanum (Ki = 3.62 mM). © 2013 Elsevier Ltd. All rights reserved. 2013 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v21_n11_p3327_Repetto http://hdl.handle.net/20.500.12110/paper_09680896_v21_n11_p3327_Repetto
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	β-d-Galactofuranosidase 6-Thiogalactofuranose Conformational analysis exo Enzyme inhibition Thiogalactofuranosyl disaccharide carbohydrate derivative disaccharide galactofuranose galactofuranosidase glycosidase methyl 6 (beta dextro galactofuranosyl) 6 thio beta dextro galactofuranoside unclassified drug article drug conformation drug synthesis enzyme inhibition mathematical analysis nuclear magnetic resonance spectroscopy Penicillium Penicillum fellutanum Antifungal Agents Carbohydrate Conformation Disaccharides Fungal Proteins Galactose Glycoside Hydrolases Glycosylation Kinetics Magnetic Resonance Spectroscopy Penicillium Thiogalactosides
spellingShingle	β-d-Galactofuranosidase 6-Thiogalactofuranose Conformational analysis exo Enzyme inhibition Thiogalactofuranosyl disaccharide carbohydrate derivative disaccharide galactofuranose galactofuranosidase glycosidase methyl 6 (beta dextro galactofuranosyl) 6 thio beta dextro galactofuranoside unclassified drug article drug conformation drug synthesis enzyme inhibition mathematical analysis nuclear magnetic resonance spectroscopy Penicillium Penicillum fellutanum Antifungal Agents Carbohydrate Conformation Disaccharides Fungal Proteins Galactose Glycoside Hydrolases Glycosylation Kinetics Magnetic Resonance Spectroscopy Penicillium Thiogalactosides Synthesis of the (1→6)-linked thiodisaccharide of galactofuranose: Inhibitory activity against a β-galactofuranosidase
topic_facet	β-d-Galactofuranosidase 6-Thiogalactofuranose Conformational analysis exo Enzyme inhibition Thiogalactofuranosyl disaccharide carbohydrate derivative disaccharide galactofuranose galactofuranosidase glycosidase methyl 6 (beta dextro galactofuranosyl) 6 thio beta dextro galactofuranoside unclassified drug article drug conformation drug synthesis enzyme inhibition mathematical analysis nuclear magnetic resonance spectroscopy Penicillium Penicillum fellutanum Antifungal Agents Carbohydrate Conformation Disaccharides Fungal Proteins Galactose Glycoside Hydrolases Glycosylation Kinetics Magnetic Resonance Spectroscopy Penicillium Thiogalactosides
description	A new (1→6)-linked thiodisaccharide formed by two galactofuranosyl units has been synthesized. Methyl (methyl α,β-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-β-d-galactofuranoside (2β) as a key precursor for the preparation of methyl per-O-tert-butyldimethylsilyl-6-thio-β-d- galactofuranoside (12). The free thiol group of 12 was glycosylated and the product O-deprotected to afford the target β-d-Galf-S-(1→6)-β-d- Galf-OMe (14). The conformations of this thiodisaccharide were preliminarily studied using combined theoretical calculations and NMR data. Furthermore, the glycomimetic 14 showed to be a competitive inhibitor of the β- galactofuranosidase from Penicillum fellutanum (Ki = 3.62 mM). © 2013 Elsevier Ltd. All rights reserved.
title	Synthesis of the (1→6)-linked thiodisaccharide of galactofuranose: Inhibitory activity against a β-galactofuranosidase
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
publishDate	2013
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v21_n11_p3327_Repetto http://hdl.handle.net/20.500.12110/paper_09680896_v21_n11_p3327_Repetto
_version_	1768544694794452992

Synthesis of the (1→6)-linked thiodisaccharide of galactofuranose: Inhibitory activity against a β-galactofuranosidase

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