Artículo
Preparation of water-soluble glycopolymers derived from five-membered iminosugars
Autor/es | Martínez Bailen, Macarena
Galbis Fuster, Elsa Carmona Asenjo, Ana Teresa Paz Báñez, María Violante de Robina Ramírez, Inmaculada |
Departamento | Universidad de Sevilla. Departamento de Química Orgánica y Farmacéutica Universidad de Sevilla. Departamento de Química orgánica |
Fecha de publicación | 2019-10 |
Fecha de depósito | 2024-01-25 |
Publicado en |
|
Resumen | Iminosugars are carbohydrate mimetics that constitute the main group of oligosaccharide processing enzyme
inhibitors. They play an important role in cell-cell recognition processes, thereby presenting a wide range ... Iminosugars are carbohydrate mimetics that constitute the main group of oligosaccharide processing enzyme inhibitors. They play an important role in cell-cell recognition processes, thereby presenting a wide range of potential therapeutic applications. In this work, we present the first examples of glycopolymers containing five-membered iminosugars. The preparation is carried out by constructing first a biocompatible water-soluble and pH-responsive 2-hydroxyethyl methacrylate (HEMA)-based copolymer by RAFT polymerization with an excellent control on the copolymer composition and low polydispersity (Mn = 19,800; Mw = 23,800; Mw/ Mn = 1.2; experimental copolymer mole composition (by 1 H NMR): pHEMA49%-co-pDMAEMA51%). One-pot azidation of its primary hydroxyl groups by Mitsunobu reaction led to a full functionalization of the HEMA residues. Subsequently, a selection of alkynyl pyrrolidine iminosugars showing glycosidase inhibition properties, were anchored to the functionalized azido-polymer through CuAAC click reaction furnishing successfully the aimed water-soluble glycopolymers, which were then subjected to biological evaluation as enzyme inhibitors. |
Agencias financiadoras | Ministerio de Economía y Competitividad (MINECO). España |
Identificador del proyecto | CTQ2016-77270-R
MAT2016-77345-C3-2P FQM-345 FQM-135 P12-FQM-1553 |
Cita | Martínez Bailen, M., Galbis Fuster, E., Carmona Asenjo, A.T., Paz Báñez, M.V.d. y Robina Ramírez, I. (2019). Preparation of water-soluble glycopolymers derived from five-membered iminosugars. European Polymer Journal, 119, 213-221. https://doi.org/10.1016/j.eurpolymj.2019.07.027. |
Ficheros | Tamaño | Formato | Ver | Descripción |
---|---|---|---|---|
2019_EurPolJ_rev_merged.pdf | 1.156Mb | [PDF] | Ver/ | Versión aceptada |