title: Synthesis of chondroitin/dermatan sulfate-like oligosaccharides and evaluation of their protein affinity by fluorescence polarization.
abstract: 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.
authors.affiliation: Glycosystems Laboratory, Instituto de Investigaciones Químicas, Centro de Investigaciones Científicas Isla de La Cartuja, CSIC and Universidad de Sevilla, Americo Vespucio, 49, 41092 Sevilla, Spain.
authors.forename: Susana
authors.initials: S
authors.lastname: Maza
authors.forename: M
authors.initials: M
authors.lastname: Mar Kayser
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Macchione
authors.forename: Javier
authors.initials: J
authors.lastname: López-Prados
authors.forename: Jesús
authors.initials: J
authors.lastname: Angulo
authors.forename: José L
authors.initials: JL
authors.lastname: de Paz
authors.forename: Pedro M
authors.initials: PM
authors.lastname: Nieto
mesh_terms: D002809:Chondroitin Sulfates / Q000138:chemical synthesis* / Q000737:chemistry; D003871:Dermatan Sulfate / Q000138:chemical synthesis* / Q000737:chemistry; D016222:Fibroblast Growth Factor 2 / Q000737:chemistry; D005454:Fluorescence Polarization; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011485:Protein Binding
chemical_list: D016222:Fibroblast Growth Factor 2; D003871:Dermatan Sulfate; D002809:Chondroitin Sulfates