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Abstract:

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.

Registro:

Documento: Artículo
Título:Synthesis of the (1→6)-linked thiodisaccharide of galactofuranose: Inhibitory activity against a β-galactofuranosidase
Autor:Repetto, E.; Marino, C.; Varela, O.
Filiación:CIHIDECAR-CONICET-UBA, Departamento de Química Orgánica, Universidad de Buenos Aires, Buenos Aires 1428, Argentina
Palabras clave: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
Año:2013
Volumen:21
Número:11
Página de inicio:3327
Página de fin:3333
DOI: http://dx.doi.org/10.1016/j.bmc.2013.02.057
Título revista:Bioorganic and Medicinal Chemistry
Título revista abreviado:Bioorg. Med. Chem.
ISSN:09680896
CODEN:BMECE
CAS:glycosidase, 9032-92-2; Antifungal Agents; Disaccharides; Fungal Proteins; Galactose, X2RN3Q8DNE; Glycoside Hydrolases, 3.2.1.-; Thiogalactosides; exo-beta-D-galactofuranosidase, 3.2.1.146; methyl 6-S-(galactofuranosyl)-6-thiogalactofuranoside
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v21_n11_p3327_Repetto

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Citas:

---------- APA ----------
Repetto, E., Marino, C. & Varela, O. (2013) . Synthesis of the (1→6)-linked thiodisaccharide of galactofuranose: Inhibitory activity against a β-galactofuranosidase. Bioorganic and Medicinal Chemistry, 21(11), 3327-3333.
http://dx.doi.org/10.1016/j.bmc.2013.02.057
---------- CHICAGO ----------
Repetto, E., Marino, C., Varela, O. "Synthesis of the (1→6)-linked thiodisaccharide of galactofuranose: Inhibitory activity against a β-galactofuranosidase" . Bioorganic and Medicinal Chemistry 21, no. 11 (2013) : 3327-3333.
http://dx.doi.org/10.1016/j.bmc.2013.02.057
---------- MLA ----------
Repetto, E., Marino, C., Varela, O. "Synthesis of the (1→6)-linked thiodisaccharide of galactofuranose: Inhibitory activity against a β-galactofuranosidase" . Bioorganic and Medicinal Chemistry, vol. 21, no. 11, 2013, pp. 3327-3333.
http://dx.doi.org/10.1016/j.bmc.2013.02.057
---------- VANCOUVER ----------
Repetto, E., Marino, C., Varela, O. Synthesis of the (1→6)-linked thiodisaccharide of galactofuranose: Inhibitory activity against a β-galactofuranosidase. Bioorg. Med. Chem. 2013;21(11):3327-3333.
http://dx.doi.org/10.1016/j.bmc.2013.02.057