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Synthesis of chondroitin/dermatan sulfate-like oligosaccharides and evaluation of their protein affinity by fluorescence polarization

AuthorsMaza, Susana ; Kayser, M. Mar ; Macchione, Giuseppe ; López-Prados, Javier; Angulo, Jesús ; de Paz, José L.; Nieto, Pedro M.
Issue Date2013
PublisherRoyal Society of Chemistry (Great Britain)
CitationOrganic and Biomolecular Chemistry 11: 3510- 3525 (2013)
AbstractHere, 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. This journal is © The Royal Society of Chemistry.
Identifiersdoi: 10.1039/c3ob40306h
issn: 1477-0520
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