Synthesis of galactofuranosyl-(1 → 5)-thiodisaccharide glycomimetics as inhibitors of a β-d-galactofuranosidase

The first synthesis of methyl β-d-galactofuranosyl-(1 → 5)-thiofuranosides is reported. These molecules, which have the 6-deoxy-5-thio derivative of l-altrofuranose (16) or d-galactofuranose (18) as the reducing end, are mimetics of the motif β-d-Galf-(1 → 5)-d-Galf found in glycoconjugates of many...

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Autores principales: Lo Fiego, M.J., Marino, C., Varela, O.
Formato: JOUR
Materias:
Conformational preferences
Galactofuranose
Glycoconjugates
Glycomimetics
Natural substrates
NMR techniques
Pathogenic microorganisms
Reducing ends
Microorganisms
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_20462069_v5_n57_p45631_LoFiego
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id todo:paper_20462069_v5_n57_p45631_LoFiego
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spelling todo:paper_20462069_v5_n57_p45631_LoFiego2023-10-03T16:38:38Z Synthesis of galactofuranosyl-(1 → 5)-thiodisaccharide glycomimetics as inhibitors of a β-d-galactofuranosidase Lo Fiego, M.J. Marino, C. Varela, O. Conformational preferences Galactofuranose Glycoconjugates Glycomimetics Natural substrates NMR techniques Pathogenic microorganisms Reducing ends Microorganisms The first synthesis of methyl β-d-galactofuranosyl-(1 → 5)-thiofuranosides is reported. These molecules, which have the 6-deoxy-5-thio derivative of l-altrofuranose (16) or d-galactofuranose (18) as the reducing end, are mimetics of the motif β-d-Galf-(1 → 5)-d-Galf found in glycoconjugates of many pathogenic microorganisms. The conformational preferences of 16 and 18 in solution were assessed by means of molecular modeling and NMR techniques. These thiodisaccharides have been evaluated as inhibitors of the β-d-galactofuranosidase from Penicillium fellutanum. The kinetics of the inhibition showed that they behave as competitive inhibitors. As expected, compound 18 (Ki = 0.15 mM), with the same configuration for the reducing end as the natural substrate of the enzyme, was a stronger inhibitor than 16 (Ki = 2.23 mM). This journal is © The Royal Society of Chemistry 2015. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_20462069_v5_n57_p45631_LoFiego
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic Conformational preferences
Galactofuranose
Glycoconjugates
Glycomimetics
Natural substrates
NMR techniques
Pathogenic microorganisms
Reducing ends
Microorganisms
spellingShingle Conformational preferences
Galactofuranose
Glycoconjugates
Glycomimetics
Natural substrates
NMR techniques
Pathogenic microorganisms
Reducing ends
Microorganisms
Lo Fiego, M.J.
Marino, C.
Varela, O.
Synthesis of galactofuranosyl-(1 → 5)-thiodisaccharide glycomimetics as inhibitors of a β-d-galactofuranosidase
topic_facet Conformational preferences
Galactofuranose
Glycoconjugates
Glycomimetics
Natural substrates
NMR techniques
Pathogenic microorganisms
Reducing ends
Microorganisms
description The first synthesis of methyl β-d-galactofuranosyl-(1 → 5)-thiofuranosides is reported. These molecules, which have the 6-deoxy-5-thio derivative of l-altrofuranose (16) or d-galactofuranose (18) as the reducing end, are mimetics of the motif β-d-Galf-(1 → 5)-d-Galf found in glycoconjugates of many pathogenic microorganisms. The conformational preferences of 16 and 18 in solution were assessed by means of molecular modeling and NMR techniques. These thiodisaccharides have been evaluated as inhibitors of the β-d-galactofuranosidase from Penicillium fellutanum. The kinetics of the inhibition showed that they behave as competitive inhibitors. As expected, compound 18 (Ki = 0.15 mM), with the same configuration for the reducing end as the natural substrate of the enzyme, was a stronger inhibitor than 16 (Ki = 2.23 mM). This journal is © The Royal Society of Chemistry 2015.
format JOUR
author Lo Fiego, M.J.
Marino, C.
Varela, O.
author_facet Lo Fiego, M.J.
Marino, C.
Varela, O.
author_sort Lo Fiego, M.J.
title Synthesis of galactofuranosyl-(1 → 5)-thiodisaccharide glycomimetics as inhibitors of a β-d-galactofuranosidase
title_short Synthesis of galactofuranosyl-(1 → 5)-thiodisaccharide glycomimetics as inhibitors of a β-d-galactofuranosidase
title_full Synthesis of galactofuranosyl-(1 → 5)-thiodisaccharide glycomimetics as inhibitors of a β-d-galactofuranosidase
title_fullStr Synthesis of galactofuranosyl-(1 → 5)-thiodisaccharide glycomimetics as inhibitors of a β-d-galactofuranosidase
title_full_unstemmed Synthesis of galactofuranosyl-(1 → 5)-thiodisaccharide glycomimetics as inhibitors of a β-d-galactofuranosidase
title_sort synthesis of galactofuranosyl-(1 → 5)-thiodisaccharide glycomimetics as inhibitors of a β-d-galactofuranosidase
url http://hdl.handle.net/20.500.12110/paper_20462069_v5_n57_p45631_LoFiego
work_keys_str_mv AT lofiegomj synthesisofgalactofuranosyl15thiodisaccharideglycomimeticsasinhibitorsofabdgalactofuranosidase
AT marinoc synthesisofgalactofuranosyl15thiodisaccharideglycomimeticsasinhibitorsofabdgalactofuranosidase
AT varelao synthesisofgalactofuranosyl15thiodisaccharideglycomimeticsasinhibitorsofabdgalactofuranosidase
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