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Abstract:

Heteroaryl 1-thio-β-D-galactofuranosides have been synthesized and evaluated as inhibitors of the exo-β-D-galactofuranosidase from Penicillium fellutanum. 2-Pyridinethiol, 4-pyridinethiol, 1-methylimidazole-2-thiol, 5-methy1-1,3,4-thiadiazole-2-thiol, 2-pyrimidinethiol and 4,6-dimethyl-2- pyrimidinethiol were employed as thiols, as such heteroaromatic aglycons are expected to display particular interactions with the active site of the enzyme. These thiols were condensed with per-O-benzoyl-D-galactofuranose, in the presence of SnCl4 or BF3.OEt2, followed by O-debenzoylation under mild conditions to afford the heteroaryl 1-thio-β-D-galactofuranosides in high yields. The enzymatic assays showed that 4,6-dimethyl-2-pyrimidyl 1-thio-β-D-galactofuranoside was the best inhibitor (IC50 135 μM), considerable more potent than the analogue lacking the methyl groups in the aglycon moiety. © ARKAT USA, Inc.

Registro:

Documento: Artículo
Título:Synthesis of heteroaryl 1-thio-β-D-galactofuranosides and evaluation of their inhibitory activity towards a β-D-galactofuranosidase
Autor:Mariño, K.; Marino, C.
Filiación:CIHIDECAR (CONICET), Departamento de Química Orgánica, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Palabras clave:Galactofuranose; Galactofuranosidase inhibitors; Glycobiology; Heteroaryl 1-thio-β-D-galactofuranosides
Año:2005
Volumen:2005
Número:12
Página de inicio:341
Página de fin:351
Título revista:Arkivoc
Título revista abreviado:Arkivoc
ISSN:14246376
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p341_Marino

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Citas:

---------- APA ----------
Mariño, K. & Marino, C. (2005) . Synthesis of heteroaryl 1-thio-β-D-galactofuranosides and evaluation of their inhibitory activity towards a β-D-galactofuranosidase. Arkivoc, 2005(12), 341-351.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p341_Marino [ ]
---------- CHICAGO ----------
Mariño, K., Marino, C. "Synthesis of heteroaryl 1-thio-β-D-galactofuranosides and evaluation of their inhibitory activity towards a β-D-galactofuranosidase" . Arkivoc 2005, no. 12 (2005) : 341-351.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p341_Marino [ ]
---------- MLA ----------
Mariño, K., Marino, C. "Synthesis of heteroaryl 1-thio-β-D-galactofuranosides and evaluation of their inhibitory activity towards a β-D-galactofuranosidase" . Arkivoc, vol. 2005, no. 12, 2005, pp. 341-351.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p341_Marino [ ]
---------- VANCOUVER ----------
Mariño, K., Marino, C. Synthesis of heteroaryl 1-thio-β-D-galactofuranosides and evaluation of their inhibitory activity towards a β-D-galactofuranosidase. Arkivoc. 2005;2005(12):341-351.
Available from: https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p341_Marino [ ]