Preparation of Water-Soluble Glycopolymers Derived from Five-Membered Iminosugars

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Preparation of Water-Soluble Glycopolymers Derived from Five-Membered Iminosugars

Inmaculada Robina 1 , Macarena Martínez-Bailén 1 , Elsa Galbis 2 , Ana T. Carmona 1 , Violante de-Paz 1

1 Department of organic Chemistry, Faculty of Chemistry, University of Seville, Seville, Spain, 2 Department of Organic and Pharmaceutical Chemistry, Faculty of Pharmacy, University of Seville, Seville, Spain

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 [1].

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 1H 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 [2] furnishing successfully the aimed water-soluble glycopolymers, which were then subjected to biological evaluation as enzyme inhibitors.

General strategy for the preparation of iminoglycopolymers via CuAAC

Kiessling, L. L., & Grim, J. C. “Glycopolymer probes of signal transduction”. Chem. Soc. Reviews, 2013, 42(10), 4476–4491.

Guo, S., Qiao, Y., Wang, W., He, H., Deng, L., Xing, J., Xu, J., Liang, X.-J. & Dong, A. “Poly(ε-caprolactone)-graft-poly(2-(N, N-dimethylamino) ethyl methacrylate) nanoparticles: pH dependent thermo-sensitive multifunctional carriers for gene and drug delivery” J. Mater. Chem., 2010, 20, 6935–6941.

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