Registro completo de metadatos
| Campo DC | Valor | Lengua/Idioma |
|---|---|---|
| dc.creator | Cagnoni, Alejandro | - |
| dc.creator | Varela, Oscar Jose | - |
| dc.creator | Kovensky, José Eduardo | - |
| dc.creator | Uhrig, Maria Laura | - |
| dc.date | 2015-09-25T17:01:19Z | - |
| dc.date | 2015-09-25T17:01:19Z | - |
| dc.date | 2013-07 | - |
| dc.date | 2016-03-30 10:35:44.97925-03 | - |
| dc.date.accessioned | 2019-04-29T15:27:18Z | - |
| dc.date.available | 2019-04-29T15:27:18Z | - |
| dc.date.issued | 2015-09-25T17:01:19Z | - |
| dc.date.issued | 2015-09-25T17:01:19Z | - |
| dc.date.issued | 2013-07 | - |
| dc.date.issued | 2016-03-30 10:35:44.97925-03 | - |
| dc.identifier | Cagnoni, Alejandro; Varela, Oscar Jose; Kovensky, José Eduardo; Uhrig, Maria Laura; Synthesis and biological activity of divalent ligands based on 3-deoxy-4-thiolactose, an isosteric analogue of lactose; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 11; 33; 7-2013; 5500-5511 | - |
| dc.identifier | 1477-0520 | - |
| dc.identifier | http://hdl.handle.net/11336/2136 | - |
| dc.identifier.uri | http://rodna.bn.gov.ar:8080/jspui/handle/bnmm/294457 | - |
| dc.description | We report here the synthesis of divalent ligands containing 3-deoxy-4-thiolactose. This thiodisaccharide has been synthesized using the Michael addition of β-1-thiogalactose to the α,β-unsaturated system of sugar-derived dihydropyranones, followed by the reduction of the remaining carbonyl group. We were able to control the configuration (S) of the stereocenter linked to sulfur (C-4) of the reducing end by conducting the thioglycosylation at high temperature or by isomerization during the reduction of the 2-ulose thiodisaccharide with NaBH4/THF. The energy profile for this reaction on a model compound was calculated. The anomeric position of the 3-deoxy-4-thiolactose was functionalized with a terminal alkyne, which was coupled to azide-containing sugar scaffolds through CuAAC reaction to afford mono- and divalent ligands. The final products were competitive inhibitors of E. coli β-galactosidase in the micromolar range. Their binding affinities to peanut agglutinin (PNA) were determined by isothermal calorimetry, which showed a clear decrease in the Ka values for monovalent derivatives compared to lactose. This report contributes to establishing the role of a particular hydroxyl group of lactose in sugarprotein recognition processes. | - |
| dc.description | Fil: Cagnoni, Alejandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina; Université de Picardie Jules Verne. Centre National de la Recherche Scientifique. Laboratoire des Glucides; Francia; | - |
| dc.description | Fil: Varela, Oscar Jose. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina; | - |
| dc.description | Fil: Kovensky, José Eduardo. Université de Picardie Jules Verne. Centre National de la Recherche Scientifique. Laboratoire des Glucides; Francia; | - |
| dc.description | Fil: Uhrig, Maria Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina; | - |
| dc.format | application/pdf | - |
| dc.format | application/pdf | - |
| dc.language | eng | - |
| dc.publisher | Royal Society of Chemistry | - |
| dc.relation | info:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/OB/2013/C3OB41074A#!divAbstract | - |
| dc.relation | info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/DOI:10.1039/C3OB41074A | - |
| dc.rights | info:eu-repo/semantics/restrictedAccess | - |
| dc.rights | https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ | - |
| dc.source | reponame:CONICET Digital (CONICET) | - |
| dc.source | instname:Consejo Nacional de Investigaciones Científicas y Técnicas | - |
| dc.source | instacron:CONICET | - |
| dc.subject | Multivalent ligands | - |
| dc.subject | Michael addition | - |
| dc.subject | Glycosidase inhibition | - |
| dc.subject | Lectin affinity | - |
| dc.subject | Química Orgánica | - |
| dc.subject | Ciencias Químicas | - |
| dc.subject | CIENCIAS NATURALES Y EXACTAS | - |
| dc.title | Synthesis and biological activity of divalent ligands based on 3-deoxy-4-thiolactose, an isosteric analogue of lactose | - |
| dc.type | info:eu-repo/semantics/article | - |
| dc.type | info:eu-repo/semantics/publishedVersion | - |
| dc.type | info:ar-repo/semantics/articulo | - |
| Aparece en las colecciones: | CONICET | |
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