Artículo
Synthesis, structure and midkine binding of chondroitin sulfate oligosaccharide analogues
Autor/es | Torres Rico, Myriam
Maza Pérez, Susana Paz Carrera, Jose Luis de Nieto Mesa, Pedro Manuel |
Fecha de publicación | 2021 |
Fecha de depósito | 2021-07-09 |
Publicado en |
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Resumen | The preparation of chondroitin sulfate (CS) oligosaccharide mimetics, more easily synthesized than natural sequences, is a highly interesting task because these compounds pave the way for modulation of the biological ... The preparation of chondroitin sulfate (CS) oligosaccharide mimetics, more easily synthesized than natural sequences, is a highly interesting task because these compounds pave the way for modulation of the biological processes in which CS is involved. Herein, we report the synthesis of CS type E analogues which present easily accessible glucose units instead of glucuronic acid (GlcA) moieties. NMR experiments and molecular dynamics simulations showed that the 3D structure of these compounds is similar to the structure of the natural CS-E oligosaccharides. In addition, fluorescence polarization (FP) and saturation transfer difference NMR (STD-NMR) experiments revealed that the synthesized CS-like derivatives were able to interact with midkine, a model heparin-binding growth factor, suggesting that the presence of the GlcA carboxylate groups is not essential for the binding. Overall, our results indicate that the synthesized glucose-containing oligosaccharides can be considered as functional and structural CS mimetics. |
Identificador del proyecto | CTQ2015-70134-P
PGC2018-099497-B100 P12-BIO-1938 |
Cita | Torres Rico, M., Maza Pérez, S., Paz Carrera, J.L.d. y Nieto Mesa, P.M. (2021). Synthesis, structure and midkine binding of chondroitin sulfate oligosaccharide analogues. Organic and Biomolecular Chemistry, 19 (24), 5312-5326. |
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