Synthesis of multivalent glycoclusters from 1-thio-β-D-galactose and their inhibitory activity against the β-galactosidase from E. coli
The synthesis of multivalent glycoclusters, designed to be compatible with biological systems, is reported. A variety of 1-thio-β-d-galactosides linked to a terminal triple bond through oligoethyleneglycol chains of variable lengths has been synthesized. Also, azide-containing oligosaccharide scaffo...
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todo:paper_00223263_v76_n9_p3064_Cagnoni2023-10-03T14:31:28Z Synthesis of multivalent glycoclusters from 1-thio-β-D-galactose and their inhibitory activity against the β-galactosidase from E. coli Cagnoni, A.J. Varela, O. Gouin, S.G. Kovensky, J. Uhrig, M.L. Azidation Biological fluids CBr Click reaction D-galactose Deacetylation E. coli Galactosidases Inhibitory activity Maltotriose NMR spectroscopy Triple bonds Valencies Variable length Acetylation Biochemistry Carbohydrates Escherichia coli Microwave irradiation Nuclear magnetic resonance spectroscopy Oligosaccharides Scaffolds Synthesis (chemical) 1 thio beta dextro galactose azide beta galactosidase carbohydrate galactose macrogol maltose oligosaccharide thioglycoside trehalose unclassified drug antibacterial activity article bioavailability chemical bond cluster analysis deacetylation drug synthesis enzyme activity Escherichia coli hydrophilicity microwave irradiation nonhuman nuclear magnetic resonance spectroscopy synthesis Alkynes Azides beta-Galactosidase Catalysis Copper Enzyme Inhibitors Escherichia coli Galactose Galactosides Polyethylene Glycols Structure-Activity Relationship Thiosugars The synthesis of multivalent glycoclusters, designed to be compatible with biological systems, is reported. A variety of 1-thio-β-d-galactosides linked to a terminal triple bond through oligoethyleneglycol chains of variable lengths has been synthesized. Also, azide-containing oligosaccharide scaffolds were prepared from trehalose, maltose, and maltotriose by direct azidation with NaN3/PPh3/CBr4. Click reaction between the thiogalactoside residues and the azide scaffolds under microwave irradiation afforded a family of glycoclusters containing 1 to 4 residues of 1-thio-β-D-galactose. The yields went from moderate to excellent, depending on the valency of the desired product. Deacetylation with Et 3N/MeOH/H2O led to the final products. Complete characterization of the products was performed by NMR spectroscopy and HR-MS techniques. Their activities as inhibitors of β-galactosidase from E. coli were determined by using the Lineweaver-Burk method. The use of hydrophilic carbohydrate scaffolds for the synthesis of multivalent galactosides represents an interesting approach to improve their pharmacokinetics and bioavailability. In addition, the presence of the thioglycosidic bond will improve their stability in biological fluids. © 2011 American Chemical Society. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00223263_v76_n9_p3064_Cagnoni |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Azidation Biological fluids CBr Click reaction D-galactose Deacetylation E. coli Galactosidases Inhibitory activity Maltotriose NMR spectroscopy Triple bonds Valencies Variable length Acetylation Biochemistry Carbohydrates Escherichia coli Microwave irradiation Nuclear magnetic resonance spectroscopy Oligosaccharides Scaffolds Synthesis (chemical) 1 thio beta dextro galactose azide beta galactosidase carbohydrate galactose macrogol maltose oligosaccharide thioglycoside trehalose unclassified drug antibacterial activity article bioavailability chemical bond cluster analysis deacetylation drug synthesis enzyme activity Escherichia coli hydrophilicity microwave irradiation nonhuman nuclear magnetic resonance spectroscopy synthesis Alkynes Azides beta-Galactosidase Catalysis Copper Enzyme Inhibitors Escherichia coli Galactose Galactosides Polyethylene Glycols Structure-Activity Relationship Thiosugars |
| spellingShingle |
Azidation Biological fluids CBr Click reaction D-galactose Deacetylation E. coli Galactosidases Inhibitory activity Maltotriose NMR spectroscopy Triple bonds Valencies Variable length Acetylation Biochemistry Carbohydrates Escherichia coli Microwave irradiation Nuclear magnetic resonance spectroscopy Oligosaccharides Scaffolds Synthesis (chemical) 1 thio beta dextro galactose azide beta galactosidase carbohydrate galactose macrogol maltose oligosaccharide thioglycoside trehalose unclassified drug antibacterial activity article bioavailability chemical bond cluster analysis deacetylation drug synthesis enzyme activity Escherichia coli hydrophilicity microwave irradiation nonhuman nuclear magnetic resonance spectroscopy synthesis Alkynes Azides beta-Galactosidase Catalysis Copper Enzyme Inhibitors Escherichia coli Galactose Galactosides Polyethylene Glycols Structure-Activity Relationship Thiosugars Cagnoni, A.J. Varela, O. Gouin, S.G. Kovensky, J. Uhrig, M.L. Synthesis of multivalent glycoclusters from 1-thio-β-D-galactose and their inhibitory activity against the β-galactosidase from E. coli |
| topic_facet |
Azidation Biological fluids CBr Click reaction D-galactose Deacetylation E. coli Galactosidases Inhibitory activity Maltotriose NMR spectroscopy Triple bonds Valencies Variable length Acetylation Biochemistry Carbohydrates Escherichia coli Microwave irradiation Nuclear magnetic resonance spectroscopy Oligosaccharides Scaffolds Synthesis (chemical) 1 thio beta dextro galactose azide beta galactosidase carbohydrate galactose macrogol maltose oligosaccharide thioglycoside trehalose unclassified drug antibacterial activity article bioavailability chemical bond cluster analysis deacetylation drug synthesis enzyme activity Escherichia coli hydrophilicity microwave irradiation nonhuman nuclear magnetic resonance spectroscopy synthesis Alkynes Azides beta-Galactosidase Catalysis Copper Enzyme Inhibitors Escherichia coli Galactose Galactosides Polyethylene Glycols Structure-Activity Relationship Thiosugars |
| description |
The synthesis of multivalent glycoclusters, designed to be compatible with biological systems, is reported. A variety of 1-thio-β-d-galactosides linked to a terminal triple bond through oligoethyleneglycol chains of variable lengths has been synthesized. Also, azide-containing oligosaccharide scaffolds were prepared from trehalose, maltose, and maltotriose by direct azidation with NaN3/PPh3/CBr4. Click reaction between the thiogalactoside residues and the azide scaffolds under microwave irradiation afforded a family of glycoclusters containing 1 to 4 residues of 1-thio-β-D-galactose. The yields went from moderate to excellent, depending on the valency of the desired product. Deacetylation with Et 3N/MeOH/H2O led to the final products. Complete characterization of the products was performed by NMR spectroscopy and HR-MS techniques. Their activities as inhibitors of β-galactosidase from E. coli were determined by using the Lineweaver-Burk method. The use of hydrophilic carbohydrate scaffolds for the synthesis of multivalent galactosides represents an interesting approach to improve their pharmacokinetics and bioavailability. In addition, the presence of the thioglycosidic bond will improve their stability in biological fluids. © 2011 American Chemical Society. |
| format |
JOUR |
| author |
Cagnoni, A.J. Varela, O. Gouin, S.G. Kovensky, J. Uhrig, M.L. |
| author_facet |
Cagnoni, A.J. Varela, O. Gouin, S.G. Kovensky, J. Uhrig, M.L. |
| author_sort |
Cagnoni, A.J. |
| title |
Synthesis of multivalent glycoclusters from 1-thio-β-D-galactose and their inhibitory activity against the β-galactosidase from E. coli |
| title_short |
Synthesis of multivalent glycoclusters from 1-thio-β-D-galactose and their inhibitory activity against the β-galactosidase from E. coli |
| title_full |
Synthesis of multivalent glycoclusters from 1-thio-β-D-galactose and their inhibitory activity against the β-galactosidase from E. coli |
| title_fullStr |
Synthesis of multivalent glycoclusters from 1-thio-β-D-galactose and their inhibitory activity against the β-galactosidase from E. coli |
| title_full_unstemmed |
Synthesis of multivalent glycoclusters from 1-thio-β-D-galactose and their inhibitory activity against the β-galactosidase from E. coli |
| title_sort |
synthesis of multivalent glycoclusters from 1-thio-β-d-galactose and their inhibitory activity against the β-galactosidase from e. coli |
| url |
http://hdl.handle.net/20.500.12110/paper_00223263_v76_n9_p3064_Cagnoni |
| work_keys_str_mv |
AT cagnoniaj synthesisofmultivalentglycoclustersfrom1thiobdgalactoseandtheirinhibitoryactivityagainstthebgalactosidasefromecoli AT varelao synthesisofmultivalentglycoclustersfrom1thiobdgalactoseandtheirinhibitoryactivityagainstthebgalactosidasefromecoli AT gouinsg synthesisofmultivalentglycoclustersfrom1thiobdgalactoseandtheirinhibitoryactivityagainstthebgalactosidasefromecoli AT kovenskyj synthesisofmultivalentglycoclustersfrom1thiobdgalactoseandtheirinhibitoryactivityagainstthebgalactosidasefromecoli AT uhrigml synthesisofmultivalentglycoclustersfrom1thiobdgalactoseandtheirinhibitoryactivityagainstthebgalactosidasefromecoli |
| _version_ |
1807322751054118912 |