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