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

Maza, Susana, Kayser, M. Mar, Macchione, Giuseppe, López-Prados, Javier, Angulo, Jesús, de Paz, José L. and Nieto, Pedro M. (2013) Synthesis of chondroitin/dermatan sulfate-like oligosaccharides and evaluation of their protein affinity by fluorescence polarization. Organic & Biomolecular Chemistry, 11 (21). pp. 3510-3525. ISSN 1477-0520

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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.

Item Type: Article
Faculty \ School: Faculty of Science > School of Pharmacy
Depositing User: Pure Connector
Date Deposited: 21 Oct 2013 19:14
Last Modified: 21 Apr 2020 22:01
URI: https://ueaeprints.uea.ac.uk/id/eprint/43771
DOI: 10.1039/c3ob40306h

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