1-Thio- -D-galactofuranosides: synthesis and evaluation as -D-galactofuranosidase inhibitors
| Autor: | Luiz Claudio Miletti, Carla Marino, Walter Colli, Karina Mariño, Maria Júlia Manso Alves, R. M. De Lederkremer |
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| Rok vydání: | 1998 |
| Předmět: | |
| Zdroj: | Glycobiology. 8:901-904 |
| ISSN: | 1460-2423 0959-6658 |
| DOI: | 10.1093/glycob/8.9.901 |
| Popis: | 2To whom correspondence should be addressed 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 penta-O-benzoyl-α,βD-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. |
| Databáze: | OpenAIRE |
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