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Abstract:

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.

Registro:

Documento: Artículo
Título:Synthesis of multivalent glycoclusters from 1-thio-β-D-galactose and their inhibitory activity against the β-galactosidase from E. coli
Autor:Cagnoni, A.J.; Varela, O.; Gouin, S.G.; Kovensky, J.; Uhrig, M.L.
Filiación:CIHIDECAR-CONICET, Departamento de Química Orgánica, Universidad de Buenos Aires, Buenos Aires, Argentina
Laboratoire des Glucides-CNRS, Université de Picardie Jules Verne, Amiens, France
Palabras clave: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
Año:2011
Volumen:76
Número:9
Página de inicio:3064
Página de fin:3077
DOI: http://dx.doi.org/10.1021/jo102421e
Título revista:Journal of Organic Chemistry
Título revista abreviado:J. Org. Chem.
ISSN:00223263
CODEN:JOCEA
CAS:azide, 12596-60-0, 14343-69-2; galactose, 26566-61-0, 50855-33-9, 59-23-4; macrogol, 25322-68-3; maltose, 16984-36-4, 69-79-4; trehalose, 99-20-7; Alkynes; Azides; Copper, 7440-50-8; Enzyme Inhibitors; Galactose, 26566-61-0; Galactosides; Polyethylene Glycols; Thiosugars; beta-Galactosidase, 3.2.1.23
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v76_n9_p3064_Cagnoni

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Citas:

---------- APA ----------
Cagnoni, A.J., Varela, O., Gouin, S.G., Kovensky, J. & Uhrig, M.L. (2011) . Synthesis of multivalent glycoclusters from 1-thio-β-D-galactose and their inhibitory activity against the β-galactosidase from E. coli. Journal of Organic Chemistry, 76(9), 3064-3077.
http://dx.doi.org/10.1021/jo102421e
---------- CHICAGO ----------
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" . Journal of Organic Chemistry 76, no. 9 (2011) : 3064-3077.
http://dx.doi.org/10.1021/jo102421e
---------- MLA ----------
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" . Journal of Organic Chemistry, vol. 76, no. 9, 2011, pp. 3064-3077.
http://dx.doi.org/10.1021/jo102421e
---------- VANCOUVER ----------
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. J. Org. Chem. 2011;76(9):3064-3077.
http://dx.doi.org/10.1021/jo102421e