Artículo

Cano, M.E.; Varela, O.; García-Moreno, M.I.; García Fernández, J.M.; Kovensky, J.; Uhrig, M.L. "Synthesis of β-galactosylamides as ligands of the peanut lectin. Insights into the recognition process" (2017) Carbohydrate Research. 443-444:58-67
El editor solo permite decargar el artículo en su versión post-print desde el repositorio. Por favor, si usted posee dicha versión, enviela a
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

The synthesis of mono and divalent β-galactosylamides linked to a hydroxylated chain having a C2 symmetry axis derived from L-tartaric anhydride is reported. Reference compounds devoid of hydroxyl groups in the linker were also prepared from β-galactosylamine and succinic anhydride. After functionalization with an alkynyl residue, the resulting building blocks were grafted onto different azide-equipped scaffolds through the copper catalyzed azide-alkyne cycloaddition. Thus, a family of structurally related mono and divalent β-N-galactopyranosylamides was obtained and fully characterized. The binding affinities of the ligands towards the model lectin PNA were measured by the enzyme-linked lectin assay (ELLA). The IC50 values were significantly higher than that of galactose but the presence of hydroxyl groups in the aglycone chain improved lectin recognition. Docking and molecular dynamics experiments were in accordance with the hypothesis that a hydroxyl group properly disposed in the linker could mimic the Glc O3 in the recognition process. On the other hand, divalent presentation of the ligands led to lectin affinity enhancements. © 2017 Elsevier Ltd

Registro:

Documento: Artículo
Título:Synthesis of β-galactosylamides as ligands of the peanut lectin. Insights into the recognition process
Autor:Cano, M.E.; Varela, O.; García-Moreno, M.I.; García Fernández, J.M.; Kovensky, J.; Uhrig, M.L.
Filiación:Universidad de Buenos Aires, Facultad de Ciencias Exactas y Naturales, Departamento de Química Orgánica, Ciudad Universitaria, Pabellón 2, Buenos Aires, C1428EHA, Argentina
Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET)-UBA, Centro de Investigación en Hidratos de Carbono (CIHIDECAR), Buenos Aires, Argentina
Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, c/ Profesor García González 1, Sevilla, 41012, Spain
Instituto de Investigaciones Químicas (IIQ), CSIC - Universidad de Sevilla, Avda. Américo Vespucio 49, Sevilla, 41092, Spain
Laboratoire de Glycochimie, des Antimicrobiens et des Agroressources (LG2A)-CNRS UMR 7378, Université de Picardie Jules Verne, 33 rue Saint Leu, Amiens Cedex, 80039, France
Palabras clave:Divalent ligands; ELLA assay; Molecular dynamics; Peanut agglutinin; β-galactosylamides; Binding energy; Chains; Chelation; Ligands; Molecular dynamics; Oilseeds; Proteins; Scaffolds; Azide-alkyne cycloaddition; Binding affinities; Functionalizations; Lectin recognition; Peanut agglutinin; Recognition process; Reference compounds; Succinic anhydride; Copper compounds; aglycone; alkyne; amide; azide; beta galactosylamide; copper; hydroxyl group; lectin; ligand; succinic anhydride; unclassified drug; galactose; ligand; peanut agglutinin; protein binding; Article; catalysis; controlled study; cycloaddition; enzymatic assay; hydroxylation; IC50; molecular docking; molecular dynamics; molecular recognition; peanut; priority journal; synthesis; chemistry; metabolism; molecular model; protein conformation; Galactose; Ligands; Models, Molecular; Peanut Agglutinin; Protein Binding; Protein Conformation
Año:2017
Volumen:443-444
Página de inicio:58
Página de fin:67
DOI: http://dx.doi.org/10.1016/j.carres.2017.03.018
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:amide, 17655-31-1; azide, 12596-60-0, 14343-69-2; copper, 15158-11-9, 7440-50-8; succinic anhydride, 108-30-5; galactose, 26566-61-0, 50855-33-9, 59-23-4; Galactose; Ligands; Peanut Agglutinin
Registro:http://digital.bl.fcen.uba.ar/collection/paper/document/paper_00086215_v443-444_n_p58_Cano

Referencias:

  • Varki, A., Cummings, R.D., Esko, J.D., Freeze, H.H., Stanley, P., Bertozzi, C.R., Hart, G.W., Etzler, M.E., (1999) Essentials of Glycobiology, 2nd Ed., , Cold Spring Harbor Laboratory Press New York
  • Lee, Y.C., Lee, R.T., (1995) Acc. Chem. Res., 28, pp. 321-327
  • Gabius, H.-J., (2009) The Sugar Code, Fundamentals of Glycosciences, , Wiley-Blackwell
  • Jiménez Blanco, J.L., Ortiz Mellet, C., García Fernández, J.M., (2013) Chem. Soc. Rev., 42, pp. 4518-4531
  • Fernández-Alonso, M.C., Díaz, D., Berbis, M.A., Marcelo, F., Cañada, J., Jiménez-Barbero, J., (2012) Curr. Prot. Pept. Sci., 13, pp. 816-830
  • Asensio, J.J., Ardá, A., Cañada, F.J., Jiménez-Barbero, J., (2013) Acc. Chem. Res., 46, pp. 946-954
  • Sharma, V., Srinivas, V.R., Adhikari, P., Vijayan, M., Surolia, A., (1998) Glycobiology, 8, pp. 1007-1012
  • Srinivas, O., Mitra, N., Surolia, A., Jayaraman, N., (2005) Glycobiology, 15, pp. 861-873
  • Swamy, M.J., Gupta, D., Mahanta, S.K., Surohat, A., (1991) Carbohydr. Res., 213, pp. 59-67
  • Lotan, R., Skutelsky, E., Danon, D., Sharon, N., (1975) J. Biol. Chem., 250, pp. 8518-8523
  • Sharma, V., Vijayan, M., Surolia, V., (1996) J. Biol. Chem., 271, pp. 21209-21213
  • Ravishankar, R., Ravindran, M., Suguna, K., Surolia, A., Vijayan, M., (1997) Curr. Sci., 72, pp. 855-861
  • Cagnoni, A.J., Kovensky, J., Uhrig, M.L., (2014) J. Org. Chem., 79, pp. 6456-6467
  • Cagnoni, A.J., Varela, O., Kovensky, J., Uhrig, M.L., (2013) Eur. J. Org. Chem., pp. 972-983
  • Cagnoni, A.J., Varela, O., Kovensky, J., Uhrig, M.L., (2013) Org. Biomol. Chem., 11, pp. 5500-5511
  • Ravishankar, R., Thomas, V., Suguna, V., Surolia, V., Vijayan, V., (2001) Proteins, 43, pp. 260-270
  • Chandrasekaran, E.V., Xue, J., Xia, J., Khaja, S.D., Piskorz, C.F., Locke, R.D., Neelamegham, S., Matta, K.L., (2016) Glycoconj. J., 33, pp. 819-836
  • Banerjee, R., Das, K., Ravishankar, R., Suguna, K., Surolia, A., Vijayan, M., (1996) J. Mol. Biol., 259, pp. 281-296
  • Mossine, V.V., Glinsky, V.V., Mawhinney, T.P., (2008) Food-related Carbohydrate Ligands for Galectins, pp. 235-270. , Galectins A.A. Klyosov Z.J. Witczak D. Platt John Wiley and Sons Hoboken, New Jersey
  • Ideo, H., Seko, A., Ohkura, T., Matta, K.L., Yamashita, K., (2002) Glycobiology, 12, pp. 199-208
  • D'Amelio, N., Esteban, C., Coslovi, A., Feruglio, L., Uggeri, F., Villegas, M., Benegas, J., Donati, I., (2013) J. Phys. Chem. B, 117, pp. 13578-13587
  • Avalos, M., Babiano, R., Carretero, M.J., Cintas, P., Higes, F.J., Jiménez, J.L., Palacios, J.C., (1998) Tetrahedron, 54, pp. 615-628
  • Masaka, R., Ogata, M., Misawa, Y., Yano, M., Hashimoto, C., Murata, T., Kawagishi, H., Usui, T., (2010) Bioorg. Med. Chem., 18, pp. 621-629
  • Vrasidas, I., André, S., Valentini, P., Böck, C., Lensch, M., Kaltner, H., Liskamp, R.M.J., Pieters, R., (2003) J. Org. Biomol. Chem., 1, pp. 803-810
  • Baussanne, I., Benito, J.M., Ortiz Mellet, C., García Fernández, J.M., Defaye, J., (2001) ChemBioChem, 2, pp. 777-783
  • André, S., Jarikote, D.V., Yan, D., Vincenz, L., Wang, G.-N., Kaltner, H., Murphy, P.V., Gabius, H.J., (2012) Bioorg. Med. Chem. Lett., 22, pp. 313-318
  • Espinosa, J.F., Cañada, F.J., Asensio, J.L., Martín-Pastor, M., Dietrich, H., Martín-Lomas, M., Schmidt, R.R., Jiménez-Barbero, J., (1996) J. Am. Chem. Soc., 118, pp. 10862-10871
  • Ravishankar, R., Surolia, A., Vijayan, M., Lim, S., Kishi, Y., (1998) J. Am. Chem. Soc., 120, pp. 11297-11303
  • Espinosa, J.F., Bruix, M., Jarreton, O., Skrydstrup, T., Beau, J.M., Jiménez-Barbero, J., (1999) Chem. Eur. J., 5, pp. 442-448
  • Jiménez-Barbero, J., Espinosa, J.F., Asensio, J.L., Cañada, F.J., Poveda, A., (2000) Adv. Carbohydr. Chem. Biochem., 56, pp. 235-284
  • García-Herrero, A., Montero, E., Muñoz, J.L., Espinosa, J.F., Vián, A., García, J.L., Asensio, J.L., Jiménez-Barbero, J., (2002) J. Am. Chem. Soc., 124, pp. 4804-4810
  • Almant, M., Mastouri, A., Gallego-Yerga, V., García Fernandez, J.M., Ortiz Mellet, C., Kovensky, J., Morandat, S., Gouin, S.G., (2013) Chem. Eur. J., 19, pp. 729-738
  • Lundquist, J.I., Toone, E., (2002) J. Chem. Rev., 102, pp. 555-578
  • Chabre, Y.M., Roy, R., (2010) Adv. Carbohydr. Chem. Biochem., 63, pp. 165-393
  • Gingras, M., Chabre, Y.M., Roy, M., Roy, R., (2013) Chem. Soc. Rev., 42, pp. 4823-4841
  • Bhatia, S., Dimde, M., Haag, R., (2014) Med. Chem. Commun., 5, pp. 862-878
  • Cecioni, S., Praly, J.P., Matthews, S.E., Wimmerov, M., Imberty, A., Vidal, S., (2012) Chem. Eur. J., 18, pp. 6250-6263
  • Sansone, F., Casnati, A., (2013) Chem. Soc. Rev., 42, pp. 4623-4639
  • Martínez, A., Ortiz Mellet, C., García Fernández, J.M., (2013) Chem. Soc. Rev., 42, pp. 4746-4773
  • Chabre, Y.M., Roy, R., (2013) Chem. Soc. Rev., 42, pp. 4657-4708
  • Zhou, C.H., Wang, Y., (2012) Curr. Med. Chem., 19, pp. 239-280
  • Morris, G.M., Goodsell, D.S., Halliday, R.S., Huey, R., Hart, W.E., Belew, R.K., Olson, A.J., (1998) J. Comput. Chem., 19, pp. 1639-1662
  • Tropper, F.D., Andersson, F.O., Braun, S., Roy, R., (1992) Synthesis, pp. 618-620
  • Ortiz Mellet, C., Méndez-Ardoy, A., García Fernández, J.M., Click multivalent glycomaterials: glycoclusters, glycopolymers, hybrid glycomaterials and glycosurfaces (2013) Click Chemistry in Glycoscience: New Developments and Strategies, pp. 143-182. , Z.J. Witczak R. Bielski Wiley New Jersey
  • Uhrig, M.L., Kovensky, J., Clicking sugars onto sugars: oligosaccharide analogues and glycoclusters on carbohydrate scaffolds (2013) Click Chemistry in Glycoscience: New Developments and Strategies, pp. 107-142. , Z.J. Witczak R. Bielski Wiley New Jersey
  • Cano, M.E., Agusti, R., Cagnoni, A.J., Tesoriero, M.F., Kovensky, J., Uhrig, M.L., Lederkremer, R.M., (2014) Beilstein J. Org. Chem., 10, pp. 3073-3086
  • Gouin, S.G., Vanquelef, E., García Fernandez, J.M., Ortíz Mellet, C., Dupradeau, F.-Y., Kovensky, J., (2007) J. Org. Chem., 72, pp. 9032-9045
  • Gouin, S.G., Wellens, A., Bouckaert, J., Kovensky, J., (2009) ChemMedChem, 4, pp. 749-755
  • Köhn, M., Benito, J.M., Ortíz Mellet, C., Lindhorst, T.K., García Fernández, J.M., (2004) ChemBioChem, 5, pp. 771-777
  • Cagnoni, A.J., Varela, O., Gouin, S.G., Kovensky, J., Uhrig, M.L., (2011) J. Org. Chem., 76, pp. 3064-3077
  • Besset, C., Pascault, J.P., Fleury, E., Drockenmuller, E., Bernard, J., (2010) Biomacromolecules, 11, pp. 2797-2803
  • Rodríguez-Lavado, J., de La Mata, M., Jiménez-Blanco, J.L., García-Moreno, M.I., Benito, J.M., Díaz-Quintana, A., Sánchez-Alcázar, J.A., García Fernández, J.M., (2014) Org. Biomol. Chem., 12, pp. 2289-2301
  • Gómez García, M., Benito, J.M., Butera, A.P., Ortiz Mellet, C., García Fernández, J.M., Jiménez Blanco, J.L., (2012) J. Org. Chem., 77, pp. 1273-1288
  • Gauto, D.F., Di Lella, S., Estrin, D.A., Monaco, H.L., Martí, M.A., (2011) Carbohydr. Res., 346, pp. 939-948
  • Gauto, D.F., Petruk, A.A., Modenutti, C.P., Blanco, J.I., Di Lella, S., Martí, M.A., (2013) Glycobiology, 23, pp. 241-258
  • Modenutti, C.P., Gauto, D.F., Radusky, L., Blanco, J.I., Turjanski, A., Hajos, S., Marti, M.A., (2015) Glycobiology, 25, pp. 181-196
  • Wittmann, V., Pieters, R.J., (2013) Chem. Soc. Rev., 42, pp. 4492-4503
  • Shriner, R.L., Furrow, C.L., Leonard, N.J., Sauers, R.R., (1955) Org. Synth., 35, p. 49
  • Ortega-Muñoz, M., Morales-Sanfrutos, J., Perez-Balderas, F., Hernández-Mateo, F., Girón-González, M.D., Sevillano-Tripero, N., Salto-González, R., Santoyo-González, F., (2007) Org. Biomol. Chem., 5, pp. 2291-2301

Citas:

---------- APA ----------
Cano, M.E., Varela, O., García-Moreno, M.I., García Fernández, J.M., Kovensky, J. & Uhrig, M.L. (2017) . Synthesis of β-galactosylamides as ligands of the peanut lectin. Insights into the recognition process. Carbohydrate Research, 443-444, 58-67.
http://dx.doi.org/10.1016/j.carres.2017.03.018
---------- CHICAGO ----------
Cano, M.E., Varela, O., García-Moreno, M.I., García Fernández, J.M., Kovensky, J., Uhrig, M.L. "Synthesis of β-galactosylamides as ligands of the peanut lectin. Insights into the recognition process" . Carbohydrate Research 443-444 (2017) : 58-67.
http://dx.doi.org/10.1016/j.carres.2017.03.018
---------- MLA ----------
Cano, M.E., Varela, O., García-Moreno, M.I., García Fernández, J.M., Kovensky, J., Uhrig, M.L. "Synthesis of β-galactosylamides as ligands of the peanut lectin. Insights into the recognition process" . Carbohydrate Research, vol. 443-444, 2017, pp. 58-67.
http://dx.doi.org/10.1016/j.carres.2017.03.018
---------- VANCOUVER ----------
Cano, M.E., Varela, O., García-Moreno, M.I., García Fernández, J.M., Kovensky, J., Uhrig, M.L. Synthesis of β-galactosylamides as ligands of the peanut lectin. Insights into the recognition process. Carbohydr. Res. 2017;443-444:58-67.
http://dx.doi.org/10.1016/j.carres.2017.03.018