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Abstract:

The sulfur linkage of β-(1→4)-thiodisaccharides was constructed with excellent diastereoselectivity by Michael addition of 2,3,4,6-tetra-O- acetyl-1-thio-β-D-galactose (2) or its β-D-glucose isomer (3) to sugar-derived (2S, 6S)-6-acetoxymethyl-2-(2-propyloxy)-2H-pyran-3(6H)-one (1). These reactions led to the per-O-acetyl glycosides of 3-deoxy-4-S- glycopyranosyl-4-thiohexopyranosid-2-ulose (4 and 5, respectively). Similar conjugated addition to the enone 1 of the isothiouronium salts 6 or 7, precursors in the synthesis of 2 or 3, also afforded the thiodisaccharides 4 or 5, respectively, with exclusive formation of the isomer that has an R configuration for the C-4 stereocenter of the reducing-end. The carbonyl function of 4 and 5 was reduced, and the resulting products were O-deacetylated to give the free 4-S(1→4)-thiodisaccharides 10, 11, 14, and 15, which have a deoxy functionality adjacent to the thio group. These compounds were tested as inhibitors of glycoside hydrolases. Thus 11, the 3-deoxy-4-thiomimetic of Galβ(1→4)Gal, proved to be a competitive inhibitor of the β-galactosidase from E. coli (K i = 0.16 mM). © Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Registro:

Documento: Artículo
Título:Stereoselective synthesis of 3-deoxy-4-S-(1→4)-thiodisaccharides and their inhibitory activities towards β-glycoside hydrolases
Autor:Uhrig, M.L.; Manzano, V.E.; Varela, O.
Filiación:CIHIDECAR-CONICET, Departamento de Química Orgánica, Ciudad Universitaria, 1428, Buenos Aires, Argentina
Palabras clave:Carbohydrates; Enzyme inhibition; Glycoside hydrolases; Michael addition; Thiodisaccharides
Año:2006
Número:1
Página de inicio:162
Página de fin:168
DOI: http://dx.doi.org/10.1002/ejoc.200500457
Título revista:European Journal of Organic Chemistry
Título revista abreviado:Eur. J. Org. Chem.
ISSN:1434193X
CODEN:EJOCF
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1434193X_v_n1_p162_Uhrig

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Citas:

---------- APA ----------
Uhrig, M.L., Manzano, V.E. & Varela, O. (2006) . Stereoselective synthesis of 3-deoxy-4-S-(1→4)-thiodisaccharides and their inhibitory activities towards β-glycoside hydrolases. European Journal of Organic Chemistry(1), 162-168.
http://dx.doi.org/10.1002/ejoc.200500457
---------- CHICAGO ----------
Uhrig, M.L., Manzano, V.E., Varela, O. "Stereoselective synthesis of 3-deoxy-4-S-(1→4)-thiodisaccharides and their inhibitory activities towards β-glycoside hydrolases" . European Journal of Organic Chemistry, no. 1 (2006) : 162-168.
http://dx.doi.org/10.1002/ejoc.200500457
---------- MLA ----------
Uhrig, M.L., Manzano, V.E., Varela, O. "Stereoselective synthesis of 3-deoxy-4-S-(1→4)-thiodisaccharides and their inhibitory activities towards β-glycoside hydrolases" . European Journal of Organic Chemistry, no. 1, 2006, pp. 162-168.
http://dx.doi.org/10.1002/ejoc.200500457
---------- VANCOUVER ----------
Uhrig, M.L., Manzano, V.E., Varela, O. Stereoselective synthesis of 3-deoxy-4-S-(1→4)-thiodisaccharides and their inhibitory activities towards β-glycoside hydrolases. Eur. J. Org. Chem. 2006(1):162-168.
http://dx.doi.org/10.1002/ejoc.200500457