dc.creator | Repetto, Evangelina | |
dc.creator | Marino, María Carla | |
dc.creator | Varela, Oscar Jose | |
dc.date.accessioned | 2015-09-24T19:40:45Z | |
dc.date.accessioned | 2018-11-06T11:30:25Z | |
dc.date.available | 2015-09-24T19:40:45Z | |
dc.date.available | 2018-11-06T11:30:25Z | |
dc.date.created | 2015-09-24T19:40:45Z | |
dc.date.issued | 2013-06-01 | |
dc.identifier | Repetto, Evangelina; Marino, María Carla; Varela, Oscar Jose; Synthesis of the (1→6)-linked thiodisaccharide of galactofuranose. Inhibitory activity against a β-galactofuranosidase; Elsevier; Bioorganic & Medicinal Chemistry; 21; 11; 1-6-2013; 3327-3333 | |
dc.identifier | 0968-0896 | |
dc.identifier | http://hdl.handle.net/11336/2107 | |
dc.identifier.uri | http://repositorioslatinoamericanos.uchile.cl/handle/2250/1853689 | |
dc.description.abstract | Methyl (methyl alpha,beta-D-galactofuranosid)uronate was employed as the starting compound,which was per-O-silylated with TBSCl and reduced with LiAlH4 to afford methyl 2,3,5-tri-O-tert-butyldimethylsilyl-b-D-galactofuranoside (2b) as akey precursor for the preparation of methyl per-O-tert-butyldimethylsilyl-6-thio-b-D-galactofuranos ide (12). The free thiol group of 12 was glycosylated and the product O-deprotected to afford the target b-D-Galf-S-(1,6)-b-D-Galf-OMe (14). The conformations of this thiodisaccharide were preliminarily studied using combined theoretical calculatio ns and NMR data.Further-more, the glycomimetic 14 showed to be a competitiv einhibitor of the beta-galactofuranosidase from Penicillum fellutanum (Ki = 3.62 mM). | |
dc.language | eng | |
dc.publisher | Elsevier | |
dc.relation | info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0968089613002551 | |
dc.relation | info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1016/j.bmc.2013.02.057 | |
dc.rights | https://creativecommons.org/licenses/by-nc-nd/2.5/ar/ | |
dc.rights | info:eu-repo/semantics/restrictedAccess | |
dc.subject | GALACTOFURANOSIDE PRECURSORS | |
dc.subject | THIOGALACTOFURANOSYL DISACCHARIDE | |
dc.subject | 6-THIOGALACTOFURANOSE | |
dc.subject | CONFORMATIONAL ANALYSIS | |
dc.subject | EXO B-D-GALACTOFURANOSIDASE | |
dc.subject | ENZYME INHIBITION | |
dc.title | Synthesis of the (1→6)-linked thiodisaccharide of galactofuranose. Inhibitory activity against a β-galactofuranosidase | |
dc.type | Artículos de revistas | |
dc.type | Artículos de revistas | |
dc.type | Artículos de revistas | |