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Abstract:

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.

Registro:

Documento: Artículo
Título:Efficient synthesis of thiolactoside glycoclusters by ruthenium-catalyzed cycloaddition reaction of disubstituted alkynes on carbohydrate scaffolds
Autor:Cagnoni, A.J.; Varela, O.; Uhrig, M.L.; Kovensky, J.
Filiación:CIHIDECAR-CONICET, Departamento de Química Orgánica, Ciudad Universitaria, Pab II, 3er piso, 1428 Ciudad de Buenos Aires, Argentina
Laboratoire des Glucides, CNRS FRE 3517, Université de Picardie Jules Verne, 33 Rue Saint Leu, 80039 Amiens, France
Palabras clave:Calorimetry; Carbohydrates; Click reaction; Glycoclusters; Glycoconjugates; Ruthenium
Año:2013
Número:5
Página de inicio:972
Página de fin:983
DOI: http://dx.doi.org/10.1002/ejoc.201201412
Título revista:European Journal of Organic Chemistry
Título revista abreviado:Eur. J. Org. Chem.
ISSN:1434193X
CODEN:EJOCF
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1434193X_v_n5_p972_Cagnoni

Referencias:

  • Chabre, Y.M., Roy, R., (2010) Adv. Carbohydr. Chem. Biochem., 63, pp. 165-393
  • Jayaraman, N., (2009) Chem. Soc. Rev., 38, pp. 3463-3483
  • Lis, H., Sharon, N., (1998) Chem. Rev., 98, pp. 637-674
  • Gabius, H.-J., André, S., Kaltner, H., Siebert, H.-C., (2002) Biochim. Biophys. Acta Gen. Subj., 1572, pp. 165-177
  • Gabius, H.-J., (2004) Adv. Drug Delivery Rev., 56, pp. 421-424
  • Ambrosi, M., Cameron, N.R., Davis, B.G., (2005) Org. Biomol. Chem., 3, pp. 1593-1608
  • Rabinovich, G.A., Toscano, M.A., Jackson, S.S., Vasta, G.R., (2007) Curr. Opin. Struct. Biol., 17, pp. 513-520
  • Flitsch, S.L., (2000) Curr. Opin. Chem. Biol., 4, pp. 619-625
  • Lee, Y.C., Lee, R.T., (1995) Acc. Chem. Res., 28, pp. 321-327
  • Mammen, M., Choi, S.-K., Whitesides, G.M., (1998) Angew. Chem., 110, pp. 2908-2953. , Angew. Chem. Int. Ed. 1998, 37, 2754 -2794
  • Lee, R.T., Lee, Y.C., (2000) Glycoconjugate J., 17, pp. 543-551
  • Lundquist, J., Toone, E.J., (2002) Chem. Rev., 102, pp. 555-578
  • Vrasidas, I., André, S., Valentini, P., Böck, C., Lensch, M., Kaltner, H., Liskamp, R.M.J., Pieters, R., (2003) Org. Biomol. Chem., 1, pp. 803-810
  • Martos, V., Castreño, P., Valero, J., De Mendoza, J., (2008) Curr. Opin. Chem. Biol., 12, pp. 698-706
  • Fletcher, S., Hamilton, A.D., (2006) J. R. Soc. Interface, 3, pp. 215-233
  • Zhou, H., Wang, D., Baldini, L., Ennis, E., Jain, R., Carie, A., Sebti, S.M., Hamilton, A.D., (2006) Org. Biomol. Chem., 4, pp. 2376-2386
  • Hershberger, S., Lee, S.-G., Chmielewski, J., (2007) Curr. Top. Med. Chem., 7, pp. 928-942
  • Tagore, D.M., Sprinz, K.I., Fletcher, S., Jayawickramarajah, J., Hamilton, A.D., (2007) Angew. Chem., 119, pp. 227-229. , Angew. Chem. Int. Ed. 2007, 46, 223 -225
  • Specker, D., Wittman, V., (2007) Top. Curr. Chem., 267, pp. 65-107
  • Röckendorf, N., Lindhorst, T.K., (2001) Top. Curr. Chem., 217, pp. 201-238
  • Bowman, M.-C., Ballard, T.E., Ackerson, C.J., Feldheim, D.L., Margolis, D.M., Melander, C., (2008) J. Am. Chem. Soc., 130, pp. 6896-6897
  • Yui, N., Ooya, T., (2006) Chem. Eur. J., 12, pp. 6730-6737
  • Chen, G., Stenzel, M.H., (2010) Polym. Chem., 1, pp. 1392-1412. , S. R. S. Ting
  • Ladmiral, V., Mantovani, G., Clarkson, G.J., Cauet, S., Irwin, J.L., Haddleton, D.M., (2006) J. Am. Chem. Soc., 128, pp. 4823-4830
  • Ortiz Mellet, C., Defaye, J., García Fernández, J.M., (2002) Chem. Eur. J., 8, pp. 1982-1990
  • Sperling, O., Fuchs, A., Lindhorst, T.K., (2006) Org. Biomol. Chem., 4, pp. 3913-3922
  • Gouin, S.G., Vanquelef, E., García Fernández, J.-M., Ortiz Mellet, C., Dupradeau, F.-Y., Kovensky, J., (2007) J. Org. Chem., 72, pp. 9032-9045
  • Ortega-Muñoz, M., Perez-Balderas, F., Morales-Sanfrutos, J., Hernández-Mateo, F., Isac-García, J., Santoyo-Gonzalez, F., (2009) Eur. J. Org. Chem., pp. 2454-2473
  • Rostovtsev, V.V., Green, L.G., Fokin, V.V., Sharpless, K.B., (2002) Angew. Chem., 114, pp. 2708-2711. , Angew. Chem. Int. Ed. 2002, 41, 2596 -2599
  • Tornoe, C.W., Christensen, C., Meldal, M., (2002) J. Org. Chem., 67, pp. 3057-3064
  • Gouin, S.G., García Fernández, J.-M., Vanquelef, E., Dupradeau, F.-Y., Salomonsson, E., Leffler, H., Ortega-Muñoz, M., Kovensky, J., (2010) ChemBioChem, 11, pp. 1430-1442
  • Gouin, S.G., Wellens, A., Bouckaert, J., Kovensky, J., (2009) ChemMedChem, 5, pp. 749-755
  • Almant, M., Moreau, V., Kovensky, J., Bouckaert, J., Gouin, S.G., (2011) Chem. Eur. J., 17, pp. 10029-10038
  • Cagnoni, A.J., Varela, O., Gouin, S.G., Kovensky, J., Uhrig, M.L., (2011) J. Org. Chem., 76, pp. 3064-3077
  • Zhang, L., Chen, X., Xue, P., Sun, H.H.Y., Williams, I.D., Sharpless, K.B., Fokin, V.V., Jia, G., (2005) J. Am. Chem. Soc., 127, pp. 15998-15999
  • Majireck, M.M., Weinreb, S.M., (2006) J. Org. Chem., 71, pp. 8680-8683
  • Boren, B.C., Narayan, S., Rasmussen, L.K., Zhang, L., Zhao, H., Lin, Z., Jia, G., Fokin, V.V., (2008) J. Am. Chem. Soc., 130, pp. 8923-8930
  • Crich, D., Yang, F., (2009) Angew. Chem., 121, pp. 9058-9061. , Angew. Chem. Int. Ed. 2009, 48, 8896 -8899
  • Salmon, A.J., Williams, M.L., Maresca, A., Supuran, C.T., Poulsen, S.-A., (2011) Bioorg. Med. Chem. Lett., 21, pp. 6058-6061
  • Baughman, T.W., Sworen, J.C., Wagener, K.B., (2004) Tetrahedron, 60, pp. 10943-10948
  • Manzano, V.E., Uhrig, M.L., Varela, O., (2008) J. Org. Chem., 73, pp. 7224-7235
  • Barenjee, R., Mande, S.C., Ganesh, V., Das, K., Dhanaraj, V., Mahanta, S.K., Suguna, K., Vijayan, M., (1994) Proc. Natl. Acad. Sci. USA, 91, pp. 227-231
  • Ravishankar, R., Thomas, C.J., Suguna, K., Surolia, A., Vijayan, M., (2001) Proteins, 43, pp. 260-270
  • Ambrosi, M., Cameron, N.R., Davis, B.G., Stolnik, S., (2005) Org. Biomol. Chem., 3, pp. 1476-1480
  • Choi, S.-K., (2004) Synthetic Multivalent Molecules. Concepts and Biomedical Aplications, , Wiley-Interscience, New Jersey, 1-22
  • Dam, T.K., Brewer, C.F., (2008) Biochemistry, 47, pp. 8470-8476
  • Fan, E., Zhang, Z., Minke, W.E., Hou, Z., Hol, W.G.J., (2000) J. Am. Chem. Soc., 122, pp. 2663-2664. , C. L. M. J. Verlinde
  • Dimick, S.M., Powell, S.C., McMahon, S.A., Moothoo, D.N., Naismith, J.H., Toone, E.J., (1999) J. Am. Chem. Soc., 121, pp. 10286-10296

Citas:

---------- APA ----------
Cagnoni, A.J., Varela, O., Uhrig, M.L. & Kovensky, J. (2013) . Efficient synthesis of thiolactoside glycoclusters by ruthenium-catalyzed cycloaddition reaction of disubstituted alkynes on carbohydrate scaffolds. European Journal of Organic Chemistry(5), 972-983.
http://dx.doi.org/10.1002/ejoc.201201412
---------- CHICAGO ----------
Cagnoni, A.J., Varela, O., Uhrig, M.L., Kovensky, J. "Efficient synthesis of thiolactoside glycoclusters by ruthenium-catalyzed cycloaddition reaction of disubstituted alkynes on carbohydrate scaffolds" . European Journal of Organic Chemistry, no. 5 (2013) : 972-983.
http://dx.doi.org/10.1002/ejoc.201201412
---------- MLA ----------
Cagnoni, A.J., Varela, O., Uhrig, M.L., Kovensky, J. "Efficient synthesis of thiolactoside glycoclusters by ruthenium-catalyzed cycloaddition reaction of disubstituted alkynes on carbohydrate scaffolds" . European Journal of Organic Chemistry, no. 5, 2013, pp. 972-983.
http://dx.doi.org/10.1002/ejoc.201201412
---------- VANCOUVER ----------
Cagnoni, A.J., Varela, O., Uhrig, M.L., Kovensky, J. Efficient synthesis of thiolactoside glycoclusters by ruthenium-catalyzed cycloaddition reaction of disubstituted alkynes on carbohydrate scaffolds. Eur. J. Org. Chem. 2013(5):972-983.
http://dx.doi.org/10.1002/ejoc.201201412