Synthesis of heteroaryl 1-thio-β-D-galactofuranosides and evaluation of their inhibitory activity towards a β-D-galactofuranosidase
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- pyrimidine...
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Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p341_Marino |
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todo:paper_14246376_v2005_n12_p341_Marino2023-10-03T16:13:43Z Synthesis of heteroaryl 1-thio-β-D-galactofuranosides and evaluation of their inhibitory activity towards a β-D-galactofuranosidase Mariño, K. Marino, C. Galactofuranose Galactofuranosidase inhibitors Glycobiology Heteroaryl 1-thio-β-D-galactofuranosides 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p341_Marino |
institution |
Universidad de Buenos Aires |
institution_str |
I-28 |
repository_str |
R-134 |
collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
topic |
Galactofuranose Galactofuranosidase inhibitors Glycobiology Heteroaryl 1-thio-β-D-galactofuranosides |
spellingShingle |
Galactofuranose Galactofuranosidase inhibitors Glycobiology Heteroaryl 1-thio-β-D-galactofuranosides Mariño, K. Marino, C. Synthesis of heteroaryl 1-thio-β-D-galactofuranosides and evaluation of their inhibitory activity towards a β-D-galactofuranosidase |
topic_facet |
Galactofuranose Galactofuranosidase inhibitors Glycobiology Heteroaryl 1-thio-β-D-galactofuranosides |
description |
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. |
format |
JOUR |
author |
Mariño, K. Marino, C. |
author_facet |
Mariño, K. Marino, C. |
author_sort |
Mariño, K. |
title |
Synthesis of heteroaryl 1-thio-β-D-galactofuranosides and evaluation of their inhibitory activity towards a β-D-galactofuranosidase |
title_short |
Synthesis of heteroaryl 1-thio-β-D-galactofuranosides and evaluation of their inhibitory activity towards a β-D-galactofuranosidase |
title_full |
Synthesis of heteroaryl 1-thio-β-D-galactofuranosides and evaluation of their inhibitory activity towards a β-D-galactofuranosidase |
title_fullStr |
Synthesis of heteroaryl 1-thio-β-D-galactofuranosides and evaluation of their inhibitory activity towards a β-D-galactofuranosidase |
title_full_unstemmed |
Synthesis of heteroaryl 1-thio-β-D-galactofuranosides and evaluation of their inhibitory activity towards a β-D-galactofuranosidase |
title_sort |
synthesis of heteroaryl 1-thio-β-d-galactofuranosides and evaluation of their inhibitory activity towards a β-d-galactofuranosidase |
url |
http://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p341_Marino |
work_keys_str_mv |
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1782031043285483520 |