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Synthesis and Characterization of Multi-Reducing-End Polysaccharides.
Zhai, Zhenghao; Zhou, Yang; Korovich, Andrew G; Hall, Brady A; Yoon, Hu Young; Yao, Yimin; Zhang, Junchen; Bortner, Michael J; Roman, Maren; Madsen, Louis A; Edgar, Kevin J.
Afiliação
  • Zhai Z; Macromolecules Innovation Institute, Virginia Tech, Blacksburg, Virginia 24061, United States.
  • Zhou Y; Department of Sustainable Biomaterials, Virginia Tech, Blacksburg, Virginia 24061, United States.
  • Korovich AG; Department of Chemistry, Macromolecules Innovation Institute, Virginia Tech, Blacksburg, Virginia 24061, United States.
  • Hall BA; GlycoMIP, Fralin Life Sciences Institute, Virginia Tech, Blacksburg, Virginia 24061, United States.
  • Yoon HY; Macromolecules Innovation Institute, Virginia Tech, Blacksburg, Virginia 24061, United States.
  • Yao Y; Department of Chemical Engineering, Macromolecules Innovation Institute, Virginia Tech, Blacksburg, Virginia 24061, United States.
  • Zhang J; Department of Biological Sciences, Virginia Tech, Blacksburg, Virginia 24061, United States.
  • Bortner MJ; Department of Chemical Engineering, Macromolecules Innovation Institute, Virginia Tech, Blacksburg, Virginia 24061, United States.
  • Roman M; Department of Sustainable Biomaterials, Macromolecules Innovation Institute, Virginia Tech, Blacksburg, Virginia 24061, United States.
  • Madsen LA; Department of Chemistry, Macromolecules Innovation Institute, Virginia Tech, Blacksburg, Virginia 24061, United States.
  • Edgar KJ; Department of Sustainable Biomaterials, Macromolecules Innovation Institute, Virginia Tech, Blacksburg, Virginia 24061, United States.
Biomacromolecules ; 24(6): 2596-2605, 2023 06 12.
Article em En | MEDLINE | ID: mdl-37262428
Site-specific modification is a great challenge for polysaccharide scientists. Chemo- and regioselective modification of polysaccharide chains can provide many useful natural-based materials and help us illuminate fundamental structure-property relationships of polysaccharide derivatives. The hemiacetal reducing end of a polysaccharide is in equilibrium with its ring-opened aldehyde form, making it the most uniquely reactive site on the polysaccharide molecule, ideal for regioselective decoration such as imine formation. However, all natural polysaccharides, whether they are branched or not, have only one reducing end per chain, which means that only one aldehyde-reactive substituent can be added. We introduce a new approach to selective functionalization of polysaccharides as an entrée to useful materials, appending multiple reducing ends to each polysaccharide molecule. Herein, we reduce the approach to practice using amide formation. Amine groups on monosaccharides such as glucosamine or galactosamine can react with carboxyl groups of polysaccharides, whether natural uronic acids like alginates, or derivatives with carboxyl-containing substituents such as carboxymethyl cellulose (CMC) or carboxymethyl dextran (CMD). Amide formation is assisted using the coupling agent 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMTMM). By linking the C2 amines of monosaccharides to polysaccharides in this way, a new class of polysaccharide derivatives possessing many reducing ends can be obtained. We refer to this class of derivatives as multi-reducing-end polysaccharides (MREPs). This new family of derivatives creates the potential for designing polysaccharide-based materials with many potential applications, including in hydrogels, block copolymers, prodrugs, and as reactive intermediates for other derivatives.
Assuntos

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Polissacarídeos / Alginatos Idioma: En Ano de publicação: 2023 Tipo de documento: Article

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Polissacarídeos / Alginatos Idioma: En Ano de publicação: 2023 Tipo de documento: Article