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

Susana Maza, M. Mar Kayser, Giuseppe Macchione, Javier López-Prados, Jesús Angulo, José L. de Paz, Pedro M. Nieto

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29 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)3510-3525
Number of pages16
JournalOrganic & Biomolecular Chemistry
Volume11
Issue number21
Early online date21 Mar 2013
DOIs
Publication statusPublished - 7 Jun 2013

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