Synthesis and characterization of alpha-d-Galp-(1-->3)-beta-d-Galp epitope-containing neoglycoconjugates for chagas disease serodiagnosis.
Lopez, R., Giorgi, M. E., Melgarejo, L. T., Ducrey, I., Balouz, V., Gonzalez-Salas, D., Camara, M. L. M., Buscaglia, C. A., de Lederkremer, R. M. and Marino, C.
Universidad de Buenos Aires. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Centro de Investigaciones en Hidratos de Carbono (CIHIDECAR). Facultad de Ciencias Exactas y Naturales. Departamento de Quimica Organica, Buenos Aires, Argentina.
Instituto de Investigaciones Biotecnologicas "Dr R. Ugalde", IIBIO, Universidad Nacional de San Martin (UNSAM) and CONICET, Buenos Aires, Argentina.
Universidad de Buenos Aires. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Centro de Investigaciones en Hidratos de Carbono (CIHIDECAR). Facultad de Ciencias Exactas y Naturales. Departamento de Quimica Organica, Buenos Aires, Argentina. Electronic address: cmarino@qo.fcen.uba.ar.
The immunodominant epitope alpha-d-Galp-(1-->3)-beta-d-Galp-(1-->4)-d-GlcNAc, expressed in the mucins of the infective trypomastigote stage of Trypanosoma cruzi has been proposed for multiple clinical applications, from serodiagnosis of protozoan caused diseases to xenotransplantation or cancer vaccinology. It was previously shown that the analogue trisaccharide, with glucose in the reducing end instead of GlcNAc, was as efficient as the natural trisaccharide for recognition of chagasic antibodies. Here we describe the synthesis of alpha-d-Galp-(1-->3)-beta-d-Galp-(1-->4)-d-Glcp functionalized as the 6-aminohexyl glycoside and its conjugation to BSA using the squarate method. The conjugate of 6-aminohexyl alpha-d-Galp-(1-->3)-beta-d-Galp was also prepared. Both neoglycoconjugates were recognized by serum samples of Trypanosoma cruzi-infected individuals and thus, are promising tools for the improvement of Chagas disease diagnostic applications.
Carbohydr Res 478: 58-67 (2019)