Efficient synthesis of thiolactoside glycoclusters by ruthenium-catalyzed cycloaddition reaction of disubstituted alkynes on carbohydrate scaffolds

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Lectin-carbohydrate interactions are responsible for several cellular processes involved in the immune system and the development of certain types of cancer. To further understanding of the cellular responses triggered by these interactions, complex carbohydrates are designed and prepared. Here, we...

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Autor principal: Cagnoni, A.J
Otros Autores: Varela, O., Uhrig, M.L, Kovensky, J.
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 2013
Acceso en línea:Registro en Scopus
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Biblioteca Central Dr. Luis F. Leloir (FCEN) de Universidad de Buenos Aires
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100 1 |a Cagnoni, A.J. 
245 1 0 |a Efficient synthesis of thiolactoside glycoclusters by ruthenium-catalyzed cycloaddition reaction of disubstituted alkynes on carbohydrate scaffolds 
260 |c 2013 
270 1 0 |m Uhrig, M.L.; CIHIDECAR-CONICET, Departamento de Química Orgánica, Ciudad Universitaria, Pab II, 3er piso, 1428 Ciudad de Buenos Aires, Argentina; email: mluhrig@qo.fcen.uba.ar 
506 |2 openaire  |e Política editorial 
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520 3 |a Lectin-carbohydrate interactions are responsible for several cellular processes involved in the immune system and the development of certain types of cancer. To further understanding of the cellular responses triggered by these interactions, complex carbohydrates are designed and prepared. Here, we describe the synthesis of a family of multivalent glycoclusters based on carbohydrate cores bearing thiolactosides or thiogalactosides as recognition elements with structural valencies ranging from 2 to 8. The synthetic strategy involves a key ruthenium-catalyzed cycloaddition reaction between symmetric disubstituted alkynes bearing two thiosugar units and azide-containing carbohydrate scaffolds. This methodology afforded high-valency glycoconjugates in good to excellent yields. Binding affinities of the synthetic β-thiolactosides for peanut lectin were measured by isothermal titration calorimetry. These titrations revealed micromolar affinities as well as a multivalent effect. A tetravalent glycoconjugate based on a trehalose scaffold displayed the highest binding affinity. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.  |l eng 
593 |a CIHIDECAR-CONICET, Departamento de Química Orgánica, Ciudad Universitaria, Pab II, 3er piso, 1428 Ciudad de Buenos Aires, Argentina 
593 |a Laboratoire des Glucides, CNRS FRE 3517, Université de Picardie Jules Verne, 33 Rue Saint Leu, 80039 Amiens, France 
690 1 0 |a CALORIMETRY 
690 1 0 |a CARBOHYDRATES 
690 1 0 |a CLICK REACTION 
690 1 0 |a GLYCOCLUSTERS 
690 1 0 |a GLYCOCONJUGATES 
690 1 0 |a RUTHENIUM 
700 1 |a Varela, O. 
700 1 |a Uhrig, M.L. 
700 1 |a Kovensky, J. 
773 0 |d 2013  |h pp. 972-983  |k n. 5  |p Eur. J. Org. Chem.  |x 1434193X  |w (AR-BaUEN)CENRE-1605  |t European Journal of Organic Chemistry 
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856 4 0 |u https://doi.org/10.1002/ejoc.201201412  |y DOI 
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