Artículo
Synthesis of chondroitin/dermatan sulfate-like oligosaccharides and evaluation of their protein affinity by fluorescence polarization
Autor/es | Maza Pérez, Susana
Kayser Gutiérrez, María del Mar Macchione, Giuseppe López Prados, Javier Angulo Álvarez, Jesús Paz Carrera, Jose Luis de |
Fecha de publicación | 2013 |
Fecha de depósito | 2018-02-20 |
Publicado en |
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Resumen | Here, we present a novel approach for the chemical synthesis of chondroitin and dermatan sulfate oligosaccharides. A key point of this strategy is the preparation and use of an N-trifluoroacetyl galactosamine building block ... Here, we present a novel approach for the chemical synthesis of chondroitin and dermatan sulfate oligosaccharides. A key point of this strategy is the preparation and use of an N-trifluoroacetyl galactosamine building block containing a 4,6-O-di-tert-butylsilylene group. Glycosylation reactions proceeded in good yields (74-91%) with our protecting group distribution. Using this approach, we have synthesized, for the first time, a chondroitin/dermatan sulfate-like tetrasaccharide that contains both types of uronic acids, d-glucuronic and l-iduronic acid. Moreover, we have employed a fluorescence polarization competition assay to evaluate the interactions between the synthesized oligosaccharides and FGF-2 (basic fibroblast growth factor). Our results show that this method, using standard instrumentation and minimal sample consumption, is a powerful tool for the rapid analysis of the glycosaminoglycan affinity for proteins in solution. |
Identificador del proyecto | CTQ2009-07168
CTQ2012-32605 P07-FQM-02969 201180E021 |
Cita | Maza Pérez, S., Kayser Gutiérrez, M.d.M., Macchione, G., López Prados, J., Angulo Álvarez, J. y Paz Carrera, J.L.d. (2013). Synthesis of chondroitin/dermatan sulfate-like oligosaccharides and evaluation of their protein affinity by fluorescence polarization. Organic and Biomolecular Chemistry, 11, 3510-3525. |
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