Thiodisaccharides with galactofuranose or arabinofuranose as terminal units: Synthesis and inhibitory activity of an exo β-d-galactofuranosidase
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 de...
Guardado en:
| Autores principales: | , , , |
|---|---|
| Formato: | JOUR |
| Materias: | |
| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_09680896_v17_n7_p2703_Repetto |
| Aporte de: |
| Sumario: | 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. |
|---|