SYNTHESIS AND CHARACTERIZATION OF GLYCOMONOMER ACRYLOYL 2,3:5,6-DI-O ISOPROPYLIDENE-α-D-MANNOFURANOSIDE
SYNTHESIS AND CHARACTERIZATION OF GLYCOMONOMER ACRYLOYL 2,3:5,6-DI-O ISOPROPYLIDENE-α-D-MANNOFURANOSIDE
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Title: | SYNTHESIS AND CHARACTERIZATION OF GLYCOMONOMER ACRYLOYL 2,3:5,6-DI-O ISOPROPYLIDENE-α-D-MANNOFURANOSIDE |
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Article_Title: | SYNTHESIS AND CHARACTERIZATION OF GLYCOMONOMER ACRYLOYL 2,3:5,6-DI-O ISOPROPYLIDENE-α-D-MANNOFURANOSIDE |
Authors: | Ioana Ramona Ciopănoiu1*, Geza-Nicolae Bandur2, Lucian-Mircea Rusnac2 |
Affiliation: | 1. Faculty of Medicine, Pharmacy and Dental Medicine, “Vasile Goldiș” Western University of Arad, 86 Liviu Rebreanu, 310045, Arad, Romania 2. Faculty of Industrial Chemistry and Environmental Engineering, “Politehnica” University of Timişoara, 6 Carol Telbisz, 300001, Timișoara, Romania |
Abstract: | Synthetic carbohydrate polymers are being increasingly investigated as biodegradable, biocompatible and biorenewable materials for use as medical devices, water absorbents or chromatographic supports. The aim of this work was to obtain a monosaccharide ester that possesses a double bond in the molecule and can thus function as a monomer. This was accomplished by reacting 2,3:5,6-diisopropylidene-D-mannofuranose with acryloyl chloride in alkaline medium and with methylene chloride as solvent, using triethylamine as capturing agent for the hydrochloric acid. The structure of the glycomonomer thus obtained was confirmed by nuclear magnetic resonance spectroscopy, Fourier transformed infrared spectroscopy and electrospray ionization mass spectrometry. |
Keywords: | glycomonomer, mannose, chemical synthesis, biorenewable, biocompatible |
References: | Cerrada ML, Sánchez-Chaves M, Ruiz C, Fernández-García M, Glycopolymers resultant from ethylene–vinyl alcohol copolymers: Degradation and rheological behavior in bulk. Eur Polym J, 44, 2194–2201, 2008 Ladmiral V, Melia E, Haddleton DM, Synthetic glycopolymers: An overview. Eur Polym J, 40, 431-449, 2004 Lichtenthaler FW, Peters S, Carbohydrates as green raw materials for the chemical industry. CR Chim, 7, 65–90, 2004 Pana AM, Rusnac LM, Bandur G, Sisu E, Badea V, Silion M, Synthesis and Characterization of New Glycopolymers based on Monosaccharides and Maleic Anhydride-I. Glucose derivatives. Mater Plast, 47(1), 28-34, 2010 Rajput VK, Mukhopadhyay B, Sulfuric acid immobilized on silica: An efficient reusable catalyst for the synthesis of O-isopropylidene sugar derivatives. Tetrahedron Lett, 47, 5939-5941, 2006 Rauter AP, Ramos-Ribeiro F, Fernandes AC, Figueiredo JA, A New Method of Acetonation with the Zeolite HY as Catalyst. Synthesis of O-Isopropylidene Sugar Derivatives. Tetrahedron, 23, 6529-6540, 1995 Sălăgean IR, Bandur G, Martin P, Lequart V, Rusnac LM, Synthesis and Characterization of Some Carbohydrate Based Monomers. Rev Chim-Bucharest, 60(9), 905-908, 2009 Sălăgean IR, Bandur G, Rusnac LM, Copolymerization of 3-O Acryloyl-1,2:5,6-di-O-Isopropylidene-α-D-Glucofuranose and Butyl Acrylate at Different Molar Ratios. Chem. Bull. “Politehnica” Univ. (Timișoara), 53(67), 69-72, 2008 Wang Q, Dordick JS, Linhardt RJ, Synthesis and Application of Carbohydrate-Containing Polymers. Chem Mater, 14, 3232-3244, 2002 Wataoka I, Kobayashi K, Kajiwara K, Effect of carbohydrate side-chain on the conformation of a glycoconjugate polystyrene in aqueous solution. Carbohyd Res, 340, 989-995,2005 |
Read_full_article: | pdf/vol16/iss1-4/7 JMA 2013 Ioana Ramona Ciopanoiu – Synthesis and characterization.pdf |
Correspondence: | Ioana Ramona Ciopănoiu, “Vasile Goldiş” Western University of Arad, Faculty of Medicine, Pharmacy and Dental Medicine, Department of Pharmaceutical Sciences, 86 Liviu Rebreanu, 310045, Arad, Romania, Tel. +40729806064, email: salageanioana@yahoo.com |
Read full article | |
Article Title: | SYNTHESIS AND CHARACTERIZATION OF GLYCOMONOMER ACRYLOYL 2,3:5,6-DI-O ISOPROPYLIDENE-α-D-MANNOFURANOSIDE |
Authors: | Ioana Ramona Ciopănoiu1*, Geza-Nicolae Bandur2, Lucian-Mircea Rusnac2 |
Affiliation: | 1. Faculty of Medicine, Pharmacy and Dental Medicine, “Vasile Goldiș” Western University of Arad, 86 Liviu Rebreanu, 310045, Arad, Romania 2. Faculty of Industrial Chemistry and Environmental Engineering, “Politehnica” University of Timişoara, 6 Carol Telbisz, 300001, Timișoara, Romania |
Abstract: | Synthetic carbohydrate polymers are being increasingly investigated as biodegradable, biocompatible and biorenewable materials for use as medical devices, water absorbents or chromatographic supports. The aim of this work was to obtain a monosaccharide ester that possesses a double bond in the molecule and can thus function as a monomer. This was accomplished by reacting 2,3:5,6-diisopropylidene-D-mannofuranose with acryloyl chloride in alkaline medium and with methylene chloride as solvent, using triethylamine as capturing agent for the hydrochloric acid. The structure of the glycomonomer thus obtained was confirmed by nuclear magnetic resonance spectroscopy, Fourier transformed infrared spectroscopy and electrospray ionization mass spectrometry. |
Keywords: | glycomonomer, mannose, chemical synthesis, biorenewable, biocompatible |
References: | Cerrada ML, Sánchez-Chaves M, Ruiz C, Fernández-García M, Glycopolymers resultant from ethylene–vinyl alcohol copolymers: Degradation and rheological behavior in bulk. Eur Polym J, 44, 2194–2201, 2008 Ladmiral V, Melia E, Haddleton DM, Synthetic glycopolymers: An overview. Eur Polym J, 40, 431-449, 2004 Lichtenthaler FW, Peters S, Carbohydrates as green raw materials for the chemical industry. CR Chim, 7, 65–90, 2004 Pana AM, Rusnac LM, Bandur G, Sisu E, Badea V, Silion M, Synthesis and Characterization of New Glycopolymers based on Monosaccharides and Maleic Anhydride-I. Glucose derivatives. Mater Plast, 47(1), 28-34, 2010 Rajput VK, Mukhopadhyay B, Sulfuric acid immobilized on silica: An efficient reusable catalyst for the synthesis of O-isopropylidene sugar derivatives. Tetrahedron Lett, 47, 5939-5941, 2006 Rauter AP, Ramos-Ribeiro F, Fernandes AC, Figueiredo JA, A New Method of Acetonation with the Zeolite HY as Catalyst. Synthesis of O-Isopropylidene Sugar Derivatives. Tetrahedron, 23, 6529-6540, 1995 Sălăgean IR, Bandur G, Martin P, Lequart V, Rusnac LM, Synthesis and Characterization of Some Carbohydrate Based Monomers. Rev Chim-Bucharest, 60(9), 905-908, 2009 Sălăgean IR, Bandur G, Rusnac LM, Copolymerization of 3-O Acryloyl-1,2:5,6-di-O-Isopropylidene-α-D-Glucofuranose and Butyl Acrylate at Different Molar Ratios. Chem. Bull. “Politehnica” Univ. (Timișoara), 53(67), 69-72, 2008 Wang Q, Dordick JS, Linhardt RJ, Synthesis and Application of Carbohydrate-Containing Polymers. Chem Mater, 14, 3232-3244, 2002 Wataoka I, Kobayashi K, Kajiwara K, Effect of carbohydrate side-chain on the conformation of a glycoconjugate polystyrene in aqueous solution. Carbohyd Res, 340, 989-995,2005 |
*Correspondence: | Ioana Ramona Ciopănoiu, “Vasile Goldiş” Western University of Arad, Faculty of Medicine, Pharmacy and Dental Medicine, Department of Pharmaceutical Sciences, 86 Liviu Rebreanu, 310045, Arad, Romania, Tel. +40729806064, email: salageanioana@yahoo.com |