Design and synthesis of vinylic glycomonomers and glycopolymer based on α-D-glucofuranose moieties
- 22 Downloads
Carbohydrates are valuable and safe sources for the synthesis of biopolymers. Today, synthetic polymers having saccharides as pedant groups are one of the great interests in biochemistry and the medicinal field. In this work, with the aim of preparing the new glyco-copolymer, firstly isopropylidene derivative of α-D-glucofuranose was synthesized from the reaction of acetone with the glucose in the presence of sulphuric acid as catalyst. Then the obtained compound separately reacted with acryloyl chloride and ρ-(chloromethyl)styrene monomers to produce related vinylic type glycomonomers. The synthesized glycomonomers were purified using column chromatography. Characterization of the synthesized vinylic glycomonomers was carried out using elemental analysis, fourier transform infrared (FT-IR), Carbon-13 nuclear magnetic resonance (13C NMR) and proton nuclear magnetic resonance (1H NMR) spectroscopy. In the next step, the obtained glycomonomers were copolymerized in 1:1 ratio via a fast and easy free radical polymerization technique. The obtained copolymer showed good solubility in various solvents such as tetrahydrofuran, chloroform, ethyl acetate, and some of the other organic solvents. Finally, water-soluble glyco-copolymer was obtained via partial hydrolysis. The structure of the isolated copolymers determined using the 1H NMR, gel permeation chromatography (GPC), and FT-IR spectroscopy.
KeywordsCarbohydrate Glycosides Biobased monomers Copolymerization Functional polymers Glyco-copolymer
Authors gratefully acknowledge the University of Tabriz and Research Center for Pharmaceutical Nanotechnology, Tabriz University of Medical Science for the financial supports for this research.
Compliance with ethical standards
Conflict of interest
The authors declare that there is no conflict of interest.
- 12.Namazi H, Salimi F (2011) Synthesis and polymerization of vinyl saccharides" as Glycomonomers" bearing 2, 3: 5, 6-Di-O-isopropylidene-α-D-mannofuranose. Iran Polym J 20(1):77–86Google Scholar
- 22.Mazăre M, Pană A, Ştefan L, Silion M, Bălan M, Bandur G, Rusnac L (2012) Novel D-glucose based Glycomonomers synthesis and characterization. World Academy of Science, Engineering and Technology, International Journal of Chemical, Molecular, Nuclear, Materials and Metallurgical Engineering 6(8):749–752Google Scholar
- 23.Rodríguez-Hernández J, Muñoz-Bonilla A, Ibarboure E, Bordegé V, Fernández-García M Honeycomb structured porous interfaces as templates for protein adhesion. In: Journal of Physics: Conference Series (2010) vol 1. IOP Publishing, p 012002Google Scholar
- 36.Matin MM, Bhuiyan MMH, Azad AKMS, Rashid MHO (2015) Synthesis of 6-O-Stearoyl-1, 2-O-isopropylidene-[alpha]-D-glucofuranose derivatives for antimicrobial evaluation. J Phys Sci 26(1):1Google Scholar
- 40.Whistler HvRL, Smith RJ, BeMiller JN, Wolfrom ML (1963) Methods in Carbohydrate Chemistry. Academic Press, New York-London:321Google Scholar