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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2015
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_20462069_v5_n57_p45631_LoFiego http://hdl.handle.net/20.500.12110/paper_20462069_v5_n57_p45631_LoFiego |
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paper:paper_20462069_v5_n57_p45631_LoFiego2023-06-08T16:33:45Z Synthesis of galactofuranosyl-(1 → 5)-thiodisaccharide glycomimetics as inhibitors of a β-d-galactofuranosidase 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. 2015 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_20462069_v5_n57_p45631_LoFiego 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 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. |
| 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 |
| publishDate |
2015 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_20462069_v5_n57_p45631_LoFiego http://hdl.handle.net/20.500.12110/paper_20462069_v5_n57_p45631_LoFiego |
| _version_ |
1768545116881944576 |