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Glycodendrimers as Chondroitin Sulfate Mimetics: Synthesis and Binding to Growth Factor Midkine
Author(s) -
DomínguezRodríguez Pedro,
Reina José J.,
GilCaballero Sergio,
Nieto Pedro M.,
de Paz José L.,
Rojo Javier
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201701890
Subject(s) - midkine , disaccharide , chemistry , chondroitin sulfate , dendrimer , glycosaminoglycan , biochemistry , chondroitin , proteoglycan , combinatorial chemistry , growth factor , extracellular matrix , receptor
Chondroitin sulfate (CS) is a member of the glycosaminoglycan (GAG) family, a class of polysaccharides implicated in relevant biological functions. The structural complexity of these carbohydrates demands the development of simple glycomimetics as useful tools to study the biological processes in which GAGs are involved. In this work we described the synthesis of the disaccharide unit of the CS‐E (GlcA‐GalNAc(4,6‐di‐OSO 3 )), in a multivalent presentation. Using a fluorescence polarization competition assay we have demonstrated that a hexavalent dendrimer of this disaccharide interact with midkine, in the low micromolar range. This result highlights the potency of these disaccharide‐displaying multivalent systems as interesting mimetics of longer and synthetically more complex GAG oligosaccharides.