Carboxyalkylation of chitosan in the gel state

Carbohydrate Polymers

Volumn 90, Issue 2, 2012, Pages 1176-1181

  Skorik, Yury A ^a,b   Pestov, Alexander V ^c   Kodess, Mikhail I ^c   Yatluk, Yury G ^c  

^a ST PETERSBURG STATE CHEMICAL PHARMACEUTICAL ACADEMY   (Russian Federation)

^b INSTITUTE OF MACROMOLECULAR COMPOUNDS   (Russian Federation)

^c INSTITUTE OF ORGANIC SYNTHESIS   (Russian Federation)

Author keywords

Carboxyalkylation; Chemical modification; Chitosan; Gel technique

Indexed keywords

AMINO GROUP; AZA-MICHAEL ADDITION; CARBOXYALKYLATION; CROTONIC ACIDS; DEGREE OF SUBSTITUTION; DILUTED SOLUTIONS; GEL STATE; GEL TECHNIQUE; PRODUCT FORMATION; SIDE REACTIONS;

ADDITION REACTIONS; CHEMICAL MODIFICATION; SUBSTITUTION REACTIONS;

CHITOSAN;

ALKYLATING AGENT; CARBON DIOXIDE; CARBOXYL RADICAL; CHITOSAN;

ALKYLATION; ARTICLE; BIOLOGICAL MODEL; CATALYSIS; CHEMISTRY; GEL; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLUTION AND SOLUBILITY;

ALKYLATING AGENTS; ALKYLATION; CARBON DIOXIDE; CATALYSIS; CHITOSAN; GELS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, BIOLOGICAL; SOLUTIONS;

EID: 84864442488     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2012.06.072     Document Type: Article

References (37)

1. N.T. An, D.T. Thien, N.T. Dong, and P. Le Dung Water-soluble N-carboxymethylchitosan derivatives: Preparation, characteristics and its application Carbohydrate Polymers 75 3 2009 489 497
2. K. Aoi, T. Seki, M. Okada, H. Sato, S. Mizutani, and H. Ohtani Synthesis of a novel N-selective ester functionalized chitin derivative and water-soluble carboxyethylchitin Macromolecular Chemistry and Physics 201 14 2000 1701 1708
3. L.Y. Chen, Z.G. Tian, and Y.M. Du Synthesis and pH sensitivity of carboxymethyl chitosan-based polyampholyte hydrogels for protein carrier matrices Biomaterials 25 17 2004 3725 3732
4. E. Chiessi, A. Palleschi, G. Paradossi, M. Venanzi, and B. Pispisa Conformational features and chelating ability of branched-chain chitosan derivatives Journal of Chemical Research-S 9 1991 248 249
5. R.E.A. Dear, and F.L. Pattison Toxic fluorine compounds. 18: Synthesis of toxic principle of dichapetalum toxicarium(18-fluoro-cis-9-octadecenoic acid) and related omega-fluoro unsaturated acids Journal of the American Chemical Society 85 5 1963 622
6. Y.M. Dong, Q. Yuan, Y.S. Wu, and M. Wang Studies on the effect of substitution degree on the liquid crystalline behavior of cyanoethyl chitosan Journal of Applied Polymer Science 76 14 2000 2057 2061
7. M. Farahani, J.M. Antonucci, and L.R. Karam A GC-MS study of the addition reaction of aryl amines with acrylic monomers Journal of Applied Polymer Science 67 9 1998 1545 1551 (Pubitemid 128562692)
8. A.I. Gamzazade, V.M. Slimak, A.M. Skljar, E.V. Stykova, S.S.A. Pavlova, and S.V. Rogozin Investigation of the hydrodynamic properties of chitosan solutions Acta Polymerica 36 8 1985 420 424
9. D.Y. Gladyshev, M.R. Bazt, G.A. Vikhoreva, L.S. Galbraikh, A.M. Ovsepyan, and Y.E. Lavut Structure and fractional composition of chitosan carboxymethyl ester Vysokomolekulyarnye Soedineniya Seriya B 32 7 1990 503 505
10. R. Jayakumar, M. Prabaharan, S.V. Nair, S. Tokura, H. Tamura, and N. Selvamurugan Novel carboxymethyl derivatives of chitin and chitosan materials and their biomedical applications Progress in Materials Science 55 7 2010 675 709
11. G. Kogan, Y.A. Skorik, I. Zitnanova, L. Krizkova, Z. Durackova, and C.A.R. Gomes Antioxidant and antimutagenic activity of N-(2-carboxyethyl) chitosan Toxicology and Applied Pharmacology 201 3 2004 303 310 (Pubitemid 39593628)
12. M. Kumar, R.A.A. Muzzarelli, C. Muzzarelli, H. Sashiwa, and A.J. Domb Chitosan chemistry and pharmaceutical perspectives Chemical Reviews 104 12 2004 6017 6084 (Pubitemid 40025733)
13. K. Kurita Controlled functionalization of the polysaccharide chitin Progress in Polymer Science 26 9 2001 1921 1971 (Pubitemid 33089088)
14. P. Ledung, M. Milas, M. Rinaudo, and J. Desbrieres Water-soluble derivatives obtained by controlled chemical modifications of chitosan Carbohydrate Polymers 24 3 1994 209 214
15. Y.M. Lee, E.M. Shin, and S.T. Noh Pervaporation separation of water-ethanol through modified chitosan membranes. 2: Carboxymethyl, carboxyethyl, cyanoethyl, and amidoxime chitosan membranes Angewandte Makromolekulare Chemie 192 1991 169 181
16. X.F. Liu, Y.L. Guan, D.Z. Yang, Z. Li, and K. De Yao Antibacterial action of chitosan and carboxymethylated chitosan Journal of Applied Polymer Science 79 7 2001 1324 1335 (Pubitemid 32138450)
17. E. Loubaki, S. Sicsic, and F. Legoffic Chemical modification of chitosan with delta-gluconolactone, beta-propiolactone and glycidol European Polymer Journal 25 4 1989 379 384 (Pubitemid 20682325)
18. R.A.A. Muzzarelli, F. Tanfani, M. Emanuelli, and S. Mariotti N-(carboxymethylidene)chitosans and N-(carboxymethyl)chitosans - Novel chelating polyampholytes obtained from chitosan glyoxylate Carbohydrate Research 107 2 1982 199 214
19. L.A. Nudga, E.A. Plisko, and S.N. Danilov Cyanoethylation of chitosan Zhurnal Obshchei Khimii 45 5 1975 1145 1149
20. A.V. Pestov, M.I. Kodess, E.G. Matochkina, and Y.G. Yatluk Selective mono-N-2-carboxyethylation of chitosan in the presence of magnesium halides Carbohydrate Polymers 86 2 2011 783 788
21. A.V. Pestov, Y.A. Skorik, G. Kogan, and Y.G. Yatluk N-alkylation of chitosan by beta-halopropionic acids in the presence of various acceptors Journal of Applied Polymer Science 108 1 2008 119 127 (Pubitemid 351363270)
22. A.V. Pestov, and Y.G. Yatluk Carboxyalkylated chitin and chitosan derivatives 2007 UB RAS Ekaterinburg
23. A.V. Pestov, N.A. Zhuravlev, and Y.G. Yatluk Synthesis in a gel as a new procedure for preparing carboxyethyl chitosan Russian Journal of Applied Chemistry 80 7 2007 1154 1159
24. M. Rinaudo Chitin and chitosan: Properties and applications Progress in Polymer Science 31 7 2006 603 632 (Pubitemid 44287019)
25. M. Rinaudo, P. Ledung, C. Gey, and M. Milas Substituent distribution on O, N-carboxymethylchitosans by H-1 NMR and C-13 NMR International Journal of Biological Macromolecules 14 3 1992 122 128
26. H. Sashiwa, N. Kawasaki, A. Nakayama, E. Muraki, H. Yajima, and N. Yamamori Chemical modification of chitosan. Part 15: Synthesis of novel chitosan derivatives by substitution of hydrophilic amine using N-carboxyethylchitosan ethyl ester as an intermediate Carbohydrate Research 338 6 2003 557 561 (Pubitemid 36351257)
27. H. Sashiwa, Y. Shigemasa, and R. Roy Chemical modification of chitosan. Part 2: Novel N-alkylation of chitosan via Michael type reaction Chemistry Letters 8 2000 862 863
28. H. Sashiwa, N. Yamamori, Y. Ichinose, J. Sunamoto, and S. Aiba Chemical modification of chitosan. 17: Michael reaction of chitosan with acrylic acid in water Macromolecular Bioscience 3 5 2003 231 233 (Pubitemid 36676084)
29. H. Sashiwa, N. Yamamori, Y. Ichinose, J. Sunamoto, and S. Aiba Michael reaction of chitosan with various acryl reagents in water Biomacromolecules 4 5 2003 1250 1254 (Pubitemid 37184637)
30. Seligsohn Gabrieli & Co. Production of alkyl esters of ypsilon-chloroalkanoic acids from butyrolactones Vol. IL55933 1978 p. 13
31. Y. Shigemasa, A. Ishida, H. Sashiwa, H. Saimoto, Y. Okamoto, and S. Minami Synthesis of a new chitin derivative, (1-carboxyethyl)chitosan Chemistry Letters 8 1995 623 624
32. Y.A. Skorik Carboxyethylated polyaminostyrene for selective copper removal Polymer Bulletin 68 4 2012 1065 1078
33. Y.A. Skorik, C.A.R. Gomes, N.V. Podberezskaya, G.V. Romanenko, L.F. Pinto, and Y.G. Yatluk Complexation models of N-(2-carboxyethyl)chitosans with copper(II) ions Biomacromolecules 6 1 2005 189 195 (Pubitemid 40277015)
34. Y.A. Skorik, C.A.R. Gomes, M. Vasconcelos, and Y.G. Yatluk N-(2-carboxyethyl)chitosans: Regioselective synthesis, characterisation and protolytic equilibria Carbohydrate Research 338 3 2003 271 276 (Pubitemid 36120704)
35. 2O Polyhedron 21 27-28 2002 2719 2725
36. S. Tokura, N. Nishi, S. Nishimura, and Y. Ikeuchi Studies on chitin. 10: Cyanoethylation of chitin Polymer Journal 15 7 1983 553 556
37. W.M. Xie, P.X. Xu, and Q. Liu Antioxidant activity of water-soluble chitosan derivatives Bioorganic and Medicinal Chemistry Letters 11 13 2001 1699 1701 (Pubitemid 32568301)