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Abstract:

Thiodisaccharides having β-d-Galf or α-l-Araf units as non-reducing end have been synthesized by the SnCl 4 - or MoO 2 Cl 2 -promoted thioglycosylation of per-O-benzoyl-d-galactofuranose (1), its 1-O-acetyl analogue 4, or per-O-acetyl-α-l-arabinofuranose (16) with 6-thioglucose or 6-thiogalactose derivatives. After convenient removal of the protecting groups, the free thiodisaccharides having the basic structure β-d-Galf(1→6)-6-thio-α-d-Glcp-OMe (5) or β-d-Galf(1→6)-6-thio-α-d-Galp-OMe (15) were obtained. The respective α-l-Araf analogues 18 and 20 were prepared similarly from 16. Alternatively, β-d-Galf(1→4)-4-thio-3-deoxy-α-l-Xylp-OiPr was synthesized by Michael addition to a sugar enone of 1-thio-β-d-Galf derivative, generated in situ from the glycosyl isothiourea derivative of 1. The free S-linked disaccharides were evaluated as inhibitors of the β-galactofuranosidase from Penicillium fellutanum, being 15 and 20 the more active inhibitors against this enzyme. © 2009 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Thiodisaccharides with galactofuranose or arabinofuranose as terminal units: Synthesis and inhibitory activity of an exo β-d-galactofuranosidase
Autor:Repetto, E.; Marino, C.; Laura Uhrig, M.; Varela, O.
Filiación:CIHIDECAR-CONICET, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Pabellon 2, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Palabras clave:Furanose; Furanosidase inhibition; Thiodisaccharides; 1 o acetyl 2,3,5,6 tetra o benzoyl beta dextro galactofuranoside; 1 o acetyl derivative; 1,2:3,4 di o isopropylidene 6 s (2,3,5,6 tetra o benzoyl dextro galactofuranosyl) 6 thio alpha dextro galactopyranose; acetic acid derivative; arabinofuranose; beta dextro galactofuranosidase; carbohydrate derivative; disaccharide; furan derivative; galactofuranose; methyl 2,3,4 tri o benzoyl 6 deoxy 6 thiocyano alpha dextro galactopyranoside; methyl 2,3,4 tri o benzoyl 6 o tosyl alpha dextro galactopyranoside; methyl 2,3,4 tri o benzoyl 6 s (2,3,5 tri o acetyl alpha levo arabinofuranosyl) 6 thio alpha dextro galactopyranoside; methyl 2,3,4 tri o benzoyl 6 s (2,3,5 tri o acetyl alpha levo arabinofuranosyl) 6 thio alpha dextro glucopyranoside; methyl 2,3,4 tri o benzoyl 6 s (2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl) 6 thio alpha dextro galactopyranoside; methyl 2,3,4 tri o benzoyl 6 s (2,3,5,6 tetra o benzoyl beta dextro galactofuranosyl) 6 thio alpha dextro glucopyranoside; methyl 2,3,4 tri o benzoyl 6 thio alpha dextro galactopyranoside; methyl 6 s (alpha levo arabinofuranosyl) 6 thio alpha dextro galactopyranoside; methyl 6 s (alpha levo arabinofuranosyl) 6 thio alpha dextro glucopyranoside; methyl 6 s (arabinose arabinofuranosyl) 6 thio alpha glucopyranoside; methyl 6 s (beta dextro galactofuranosyl) 6 thio alpha dextro galactopyranoside; methyl 6 s (beta dextro galactofuranosyl) 6 thio alpha dextro glucopyranoside; unclassified drug; article; carbohydrate synthesis; enzyme activity; enzyme inhibition; enzyme synthesis; glycosylation; Michael addition; Penicillium; Penicillium fellutanum; Arabinose; Catalysis; Chlorine Compounds; Disaccharides; Enzyme Inhibitors; Galactose; Glycoside Hydrolases; Manganese Compounds; Oxides; Penicillium; Sulfides; Tin Compounds; Penicillium fellutanum
Año:2009
Volumen:17
Número:7
Página de inicio:2703
Página de fin:2711
DOI: http://dx.doi.org/10.1016/j.bmc.2009.02.045
Título revista:Bioorganic and Medicinal Chemistry
Título revista abreviado:Bioorg. Med. Chem.
ISSN:09680896
CODEN:BMECE
CAS:Arabinose, 147-81-9; Chlorine Compounds; Disaccharides; Enzyme Inhibitors; Galactose, 26566-61-0; Glycoside Hydrolases, 3.2.1.-; Manganese Compounds; MoO2Cl2; Oxides; Sulfides; Tin Compounds; arabinofuranose; exo-beta-D-galactofuranosidase, 3.2.1.146; stannic chloride, 7646-78-8
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v17_n7_p2703_Repetto

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Citas:

---------- APA ----------
Repetto, E., Marino, C., Laura Uhrig, M. & Varela, O. (2009) . Thiodisaccharides with galactofuranose or arabinofuranose as terminal units: Synthesis and inhibitory activity of an exo β-d-galactofuranosidase. Bioorganic and Medicinal Chemistry, 17(7), 2703-2711.
http://dx.doi.org/10.1016/j.bmc.2009.02.045
---------- CHICAGO ----------
Repetto, E., Marino, C., Laura Uhrig, M., Varela, O. "Thiodisaccharides with galactofuranose or arabinofuranose as terminal units: Synthesis and inhibitory activity of an exo β-d-galactofuranosidase" . Bioorganic and Medicinal Chemistry 17, no. 7 (2009) : 2703-2711.
http://dx.doi.org/10.1016/j.bmc.2009.02.045
---------- MLA ----------
Repetto, E., Marino, C., Laura Uhrig, M., Varela, O. "Thiodisaccharides with galactofuranose or arabinofuranose as terminal units: Synthesis and inhibitory activity of an exo β-d-galactofuranosidase" . Bioorganic and Medicinal Chemistry, vol. 17, no. 7, 2009, pp. 2703-2711.
http://dx.doi.org/10.1016/j.bmc.2009.02.045
---------- VANCOUVER ----------
Repetto, E., Marino, C., Laura Uhrig, M., Varela, O. Thiodisaccharides with galactofuranose or arabinofuranose as terminal units: Synthesis and inhibitory activity of an exo β-d-galactofuranosidase. Bioorg. Med. Chem. 2009;17(7):2703-2711.
http://dx.doi.org/10.1016/j.bmc.2009.02.045