Selective mono-N-2-carboxyethylation of chitosan in the presence of magnesium halides

Carbohydrate Polymers

Volumn 86, Issue 2, 2011, Pages 783-788

  Pestov, Alexander V ^a   Kodess, Mikhail I ^a   Matochkina, Evgeniya G ^a   Yatluk, Yury G ^a  

^a INSTITUTE OF ORGANIC SYNTHESIS   (Russian Federation)

Author keywords

2 Carboxyethylation; Chitosan; Functionalization of polymer; Selectivity

Indexed keywords

2-CARBOXYETHYLATION; ACRYLIC ACIDS; AMINO GROUP; DEGREE OF SUBSTITUTION; FUNCTIONALIZATION OF POLYMER; H NMR SPECTROSCOPY; MAGNESIUM HALIDES; SELECTIVE PRODUCTION;

CARBOXYLIC ACIDS; FUNCTIONAL POLYMERS; LITHIUM; MAGNESIUM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS (CHEMICAL);

CHITOSAN;

EID: 79960557015     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2011.05.023     Document Type: Article

References (20)

1. S.N. Chirkov The antiviral activity of chitosan Applied Biochemistry and Microbiology 38 2002 1 8 (in review)
2. A.I. Gamzazade, V.M. Slimak, A.M. Skljar, E.V. Stykova, S.A. Pavlova, and S.V. Rogozin Investigation of the hydrodynamic properties of chitosan solutions Acta Polymerica 36 1985 420 424
3. H. Jiang, Y. Wang, Q. Huang, Y. Li, C. Xu, and K. Zhu Biodegradable hyaluronic acid/N-carboxyethyl chitosan/protein ternary complexes as implantable carriers for controlled protein release Macromolecular Bioscience 5 2005 1226 1233 (Pubitemid 43015297)
4. G. Kogan, Yu.A. Skorik, I. Žitňanova, L. Križkova, Z. Ďuračkova, and C.A.R. Gomes Antioxidant and antimutagenic activity of N-(2-carboxyethyl)chitosan Toxicology and Applied Pharmacology 201 2004 303 310 (Pubitemid 39593628)
5. M.N.V.R. Kumar, R.A.A. Muzzarelli, C. Muzzarelli, H. Sashiwa, and A.J. Domb Chitosan chemistry and pharmaceutical perspectives Chemical Reviews 104 2004 6017 6084 (Pubitemid 40025733)
6. X.F. Liu, Y.L. Guan, D.Z. Yang, Z. Li, and K.D. Yao Antibacterial action of chitosan and carboxymethylated chitosan Journal of Applied Polymer Science 79 2001 1324 1335 (Pubitemid 32138450)
7. R. Mincheva, N. Manolova, D. Paneva, and I. Rashkov Preparation of polyelectrolyte-containing nanofibers by electrospinning in the presence of a non-ionogenic water-soluble polymer Journal of Bioactive and Compatible Polymers 20 2005 419 435 (Pubitemid 41375526)
8. R. Mincheva, N. Manolova, D. Paneva, and I. Rashkov Novel polyelectrolyte complexes between N-carboxyethylchitosan and synthetic polyelectrolytes European Polymer Journal 42 2006 858 868 (Pubitemid 43344428)
9. I. Orienti, B. Luppi, and V. Zecchi Chitosan and its N-carboxyethyl and N-aminoethyl derivatives as vehicles for topical formulation Journal of Cosmetical Science 50 1999 307 313
10. A.V. Pestov, G. Kogan, Yu.A Skorik, Yu.G. Yatluk, and M. Pajtinka Symposium on polymer architecture "From Structure to Functional control" Budapest, Hungary, 2006 August 30-September 1 2006 23
11. A.V. Pestov, Yu.A. Skorik, G. Kogan, and Yu.G. Yatluk N-alkylation of chitosan by β-halopropionic acids in the presence of various acceptors Journal of Applied Polymer Science 108 2008 119 127 (Pubitemid 351363270)
12. A.V. Pestov, N.A. Zhuravlev, and Yu.G. Yatluk Synthesis in a gel as a new procedure for preparing carboxyethyl chitosan Russian Journal of Applied Chemistry 80 2007 1154 1159
13. E.I. Rabea, M.E.-T. Badawy, C.V. Stevens, G. Smagghe, and W. Steurbaut Chitosan as antimicrobial agent: Applications and mode of action Biomacromolecules 4 2003 1457 1465 (Pubitemid 37455555)
14. V.N. Salov, E.N. Zil'berman, and V.L. Krasnov Interaction of acrylic-acid with amines in aqueous-solutions Izvestiya Vysshikh Uchebnykh Zavedenii, Khimiya i Khimicheskaya Tekhnologiya 28 1985 21 25
15. a Michael reaction of chitosan with acrylic acid in water Macromolecular Bioscience 3 2003 231 233 (Pubitemid 36676084)
16. Y. Shigemasa, H. Usui, M. Morimoto, H. Saimoto, Y. Okamoto, and S. Minami Chemical modification of chitin and chitosan 1: Preparation of partially deacetylated chitin derivatives via a ring-opening reaction with cyclic acid anhydrides in lithium chloride/N,N-dimethylacetamide Carbohydrate Polymers 39 1999 237 243 (Pubitemid 129750812)
17. Yu.A. Skorik, C.A.R. Gomes, T.M.S.D. Vasconcelos, and Yu.G. Yatluk N-(2-Carboxyethyl)chitosans: Regioselective synthesis, characterisation and protolytic equilibria Carbohydrate Research 338 2003 271 276 (Pubitemid 36120704)
18. Tokura, S., & Seo, H. (1994). Chitin solution. Jap. Patent 6179702A.
19. A.J. Varma, S.V. Deshpande, and J.F. Kennedy Metal complexation by chitosan and its derivatives: A review Carbohydrate Polymers 55 2004 77 93
20. L. Weng, A. Romanov, J. Rooney, and W. Chen Non-cytotoxic, in situ gelable hydrogels composed of N-carboxyethyl chitosan and oxidized dextran Biomaterials 29 2008 3905 3913