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Título: | Fluorous-tag assisted synthesis of a glycosaminoglycan mimetic tetrasaccharide as a high-affinity FGF-2 and midkine ligand |
Autor: | Maza, Susana CSIC; Gandia-Aguado, Noel; Paz, José L. de CSIC ORCID; Nieto, Pedro M. CSIC ORCID | Fecha de publicación: | 2018 | Editor: | Pergamon Press | Citación: | Bioorganic and Medicinal Chemistry 26: 1076- 1085 (2018) | Resumen: | Here, we present the preparation of a sulfated, fully protected tetrasaccharide derivative following the glycosaminoglycan (GAG)-related sequence GlcNAc-β(1 → 4)-Glc-β(1 → 3). The tetramer was efficiently assembled via an iterative glycosylation strategy using monosaccharide building blocks. A fluorous tag was attached at position 6 of the reducing end unit enabling the purification of reaction intermediates by simple fluorous solid phase extraction. Fluorescence polarization competition experiments revealed that the synthesized tetrasaccharide strongly interacts with two heparin-binding growth factors, midkine and FGF-2 (IC of 270 nM and 2.4 µM, respectively). Our data indicate that this type of oligosaccharide derivatives, displaying sulfates, hydrophobic protecting groups and a fluorinated tail can be considered as interesting GAG mimetics for the regulation of relevant carbohydrate-protein interactions. | URI: | http://hdl.handle.net/10261/170027 | DOI: | 10.1016/j.bmc.2018.01.022 | Identificadores: | doi: 10.1016/j.bmc.2018.01.022 issn: 1464-3391 |
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