1-Thio-β-D-galactofuranosides: Synthesis and evaluation as β-D-galactofuranosidase inhibitors
β-D-galactofuranosidase is a good chemotherapeutic target for the design of inhibitors, since β-D-galactofuranose is a constituent of important parasite glycoconjugates but is not present in the host mammals. With this aim, we have synthesized for the first time alkyl, benzyl and aryl 1-thio-β-D-gal...
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1998
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09596658_v8_n9_p901_Marino http://hdl.handle.net/20.500.12110/paper_09596658_v8_n9_p901_Marino |
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paper:paper_09596658_v8_n9_p901_Marino2023-06-08T15:57:07Z 1-Thio-β-D-galactofuranosides: Synthesis and evaluation as β-D-galactofuranosidase inhibitors Affinity ligands Galactofuranose Galactofuranosidase inhibitors thio-β-D-galactofuranosides galactofuranosidase galactofuranoside derivative unclassified drug affinity chromatography article controlled study drug synthesis enzyme isolation hydrogenation nonhuman priority journal stereochemistry Mammalia Penicillium fellutanum β-D-galactofuranosidase is a good chemotherapeutic target for the design of inhibitors, since β-D-galactofuranose is a constituent of important parasite glycoconjugates but is not present in the host mammals. With this aim, we have synthesized for the first time alkyl, benzyl and aryl 1-thio-β-D-galactofuranosides by condensation of pent-O-benzoyl-α,β-D-galactofuranose with the corresponding thiols, in the presence of SnCl4 as catalyst. The complete chemical and spectroscopical characterization of these compounds showed that the reaction was stereoselective. Debenzoylation with sodium methoxide afforded the β-S-galactofuranosides in high yield. The thioglycosides were tested as inhibitors of the β-D-galactofuranosidase of Penicillium fellutanum, using for the first time 4-nitrophenyl-β-D-galactofuranoside as chromogenic substrate. The 4-aminophenyl-1-thio-β-D-galactofuranoside, obtained by catalytic hydrogenation of the nitrophenyl derivative, was the best inhibitor being then an adequate ligand for the preparation of an affinity phase aimed at the isolation of β-D-galactofuranosidases from different sources. Also the inhibitory activity of D-galactono-1,4-lactone was shown. 1998 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09596658_v8_n9_p901_Marino http://hdl.handle.net/20.500.12110/paper_09596658_v8_n9_p901_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 |
Affinity ligands Galactofuranose Galactofuranosidase inhibitors thio-β-D-galactofuranosides galactofuranosidase galactofuranoside derivative unclassified drug affinity chromatography article controlled study drug synthesis enzyme isolation hydrogenation nonhuman priority journal stereochemistry Mammalia Penicillium fellutanum |
| spellingShingle |
Affinity ligands Galactofuranose Galactofuranosidase inhibitors thio-β-D-galactofuranosides galactofuranosidase galactofuranoside derivative unclassified drug affinity chromatography article controlled study drug synthesis enzyme isolation hydrogenation nonhuman priority journal stereochemistry Mammalia Penicillium fellutanum 1-Thio-β-D-galactofuranosides: Synthesis and evaluation as β-D-galactofuranosidase inhibitors |
| topic_facet |
Affinity ligands Galactofuranose Galactofuranosidase inhibitors thio-β-D-galactofuranosides galactofuranosidase galactofuranoside derivative unclassified drug affinity chromatography article controlled study drug synthesis enzyme isolation hydrogenation nonhuman priority journal stereochemistry Mammalia Penicillium fellutanum |
| description |
β-D-galactofuranosidase is a good chemotherapeutic target for the design of inhibitors, since β-D-galactofuranose is a constituent of important parasite glycoconjugates but is not present in the host mammals. With this aim, we have synthesized for the first time alkyl, benzyl and aryl 1-thio-β-D-galactofuranosides by condensation of pent-O-benzoyl-α,β-D-galactofuranose with the corresponding thiols, in the presence of SnCl4 as catalyst. The complete chemical and spectroscopical characterization of these compounds showed that the reaction was stereoselective. Debenzoylation with sodium methoxide afforded the β-S-galactofuranosides in high yield. The thioglycosides were tested as inhibitors of the β-D-galactofuranosidase of Penicillium fellutanum, using for the first time 4-nitrophenyl-β-D-galactofuranoside as chromogenic substrate. The 4-aminophenyl-1-thio-β-D-galactofuranoside, obtained by catalytic hydrogenation of the nitrophenyl derivative, was the best inhibitor being then an adequate ligand for the preparation of an affinity phase aimed at the isolation of β-D-galactofuranosidases from different sources. Also the inhibitory activity of D-galactono-1,4-lactone was shown. |
| title |
1-Thio-β-D-galactofuranosides: Synthesis and evaluation as β-D-galactofuranosidase inhibitors |
| title_short |
1-Thio-β-D-galactofuranosides: Synthesis and evaluation as β-D-galactofuranosidase inhibitors |
| title_full |
1-Thio-β-D-galactofuranosides: Synthesis and evaluation as β-D-galactofuranosidase inhibitors |
| title_fullStr |
1-Thio-β-D-galactofuranosides: Synthesis and evaluation as β-D-galactofuranosidase inhibitors |
| title_full_unstemmed |
1-Thio-β-D-galactofuranosides: Synthesis and evaluation as β-D-galactofuranosidase inhibitors |
| title_sort |
1-thio-β-d-galactofuranosides: synthesis and evaluation as β-d-galactofuranosidase inhibitors |
| publishDate |
1998 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09596658_v8_n9_p901_Marino http://hdl.handle.net/20.500.12110/paper_09596658_v8_n9_p901_Marino |
| _version_ |
1768546168601575424 |