Maza Pérez, SusanaKayser Gutiérrez, María del MarMacchione, GiuseppeLópez Prados, JavierAngulo Álvarez, JesúsPaz Carrera, Jose Luis de2018-02-202018-02-202013Maza 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, 3510-3525.1477-0520https://hdl.handle.net/11441/70453Here, 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.application/pdfengAttribution-NonCommercial-NoDerivatives 4.0 Internacionalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/articleinfo:eu-repo/semantics/openAccesshttps://doi.org/10.1039/c3ob40306h