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Abstract:

The ring-opening reaction of sugar 3,4-epoxides by 2,3,4,6-tetra-O-acetyl- 1-thio-β-d-galactopyranose (7) as a nucleophile led to (1 → 3)- and (1 → 4)-thiodisaccharides. High regio- and diastereoselectivities were achieved in the synthesis of the per-O-acetyl derivative of the β-d-Galp-S-(1 → 4)-4-thio-α-d-Glcp-O-iPr (10). Analogues of the 4-thiolactoside 10 have been prepared, with the β-d-Galp non-reducing end S-linked to d-Glcp, d-Gulp and d-Idop. A similar regioselective attack of 7 on C-4 of 2-propyl 3,6-di-O-acetyl-3,4-epithio-α-d-galactopyranoside (6) led to 2-propyl 3,4-dithiolactoside derivative 15. During this reaction the free 3-SH group of 15 underwent oxidative dimerization or oxidative coupling with the SH function of 7 to give the respective disulfides. Glycosylation of the thiol group of 15 using trichloroacetimidate derivatives of β-d-Galp or β-d-Galf afforded the corresponding branched dithiotrisaccharides. The free compounds were evaluated as inhibitors of the E. coli β-galactoside. The bis(2-propyl 3,4-dithiolactosid-3-yl)-disulfide, obtained from 15, displayed the strongest inhibitory activity in these series of glycomimetics and proved to be a non-competitive inhibitor (Ki = 95 μM). © 2012 The Royal Society of Chemistry.

Registro:

Documento: Artículo
Título:Convenient synthesis of 4-thiolactose, 3,4-dithiolactose and related thiooligosaccharides and disulfides. Inhibitory activity of the glycomimetics against a β-galactosidase
Autor:Manzano, V.E.; Uhrig, M.L.; Varela, O.
Filiación:CIHIDECAR-CONICET-UBA, Departamento de Química Orgánica, Ciudad Universitaria, Pabellón II, 1428-Buenos Aires, Argentina
Año:2012
Volumen:10
Número:44
Página de inicio:8884
Página de fin:8894
DOI: http://dx.doi.org/10.1039/c2ob26388b
Título revista:Organic and Biomolecular Chemistry
Título revista abreviado:Org. Biomol. Chem.
ISSN:14770520
CODEN:OBCRA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14770520_v10_n44_p8884_Manzano

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Citas:

---------- APA ----------
Manzano, V.E., Uhrig, M.L. & Varela, O. (2012) . Convenient synthesis of 4-thiolactose, 3,4-dithiolactose and related thiooligosaccharides and disulfides. Inhibitory activity of the glycomimetics against a β-galactosidase. Organic and Biomolecular Chemistry, 10(44), 8884-8894.
http://dx.doi.org/10.1039/c2ob26388b
---------- CHICAGO ----------
Manzano, V.E., Uhrig, M.L., Varela, O. "Convenient synthesis of 4-thiolactose, 3,4-dithiolactose and related thiooligosaccharides and disulfides. Inhibitory activity of the glycomimetics against a β-galactosidase" . Organic and Biomolecular Chemistry 10, no. 44 (2012) : 8884-8894.
http://dx.doi.org/10.1039/c2ob26388b
---------- MLA ----------
Manzano, V.E., Uhrig, M.L., Varela, O. "Convenient synthesis of 4-thiolactose, 3,4-dithiolactose and related thiooligosaccharides and disulfides. Inhibitory activity of the glycomimetics against a β-galactosidase" . Organic and Biomolecular Chemistry, vol. 10, no. 44, 2012, pp. 8884-8894.
http://dx.doi.org/10.1039/c2ob26388b
---------- VANCOUVER ----------
Manzano, V.E., Uhrig, M.L., Varela, O. Convenient synthesis of 4-thiolactose, 3,4-dithiolactose and related thiooligosaccharides and disulfides. Inhibitory activity of the glycomimetics against a β-galactosidase. Org. Biomol. Chem. 2012;10(44):8884-8894.
http://dx.doi.org/10.1039/c2ob26388b