Synthesis of carboxyl cellulose sulfate with various contents of regioselectively introduced sulfate and carboxyl groups

Carbohydrate Polymers

Volumn 82, Issue 1, 2010, Pages 92-99

  Zhang, Kai ^a   Peschel, Dieter ^b   Klinger, Thomas ^c   Gebauer, Kathrin ^a   Groth, Thomas ^b   Fischer, Steffen ^a  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

^b MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

^c Institute of Soil Science and Site Ecology   (Germany)

Author keywords

13C NMR spectroscopy; Carboxyl cellulose; Carboxyl cellulose sulfate; Cellulose sulfate; FT Raman spectroscopy

Indexed keywords

ANALYSIS METHOD; ANHYDROGLUCOSE UNIT; BIOLOGICAL ACTIVITIES; CARBOXYL CELLULOSE SULFATE; CARBOXYL GROUPS; CELLULOSE SULFATES; FT- RAMAN SPECTROSCOPY; GLYCOSAMINOGLYCANS; NMR SPECTROSCOPY; SYNTHESIS ROUTE; TEMPO-MEDIATED OXIDATION;

BIOACTIVITY; FUNCTIONAL GROUPS; GROUP TECHNOLOGY; MOLECULAR VIBRATIONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; RAMAN SCATTERING; RAMAN SPECTROSCOPY;

CELLULOSE;

CARBOXYLATION; CELLULOSE SULFATE; FUNCTIONAL GROUPS; NUCLEAR MAGNETIC RESONANCE; OXIDATION; RAMAN SPECTROSCOPY;

EID: 77953917144     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2010.04.027     Document Type: Article

References (46)

1. Alban S., Schauerte A., and Franz G. Anticoagulant sulphated polysaccharides: Part I. Synthesis and structure-activity relationships of new pullulan sulphates. Carbohydrate Polymers 47 (2002) 267-276
2. American Society for Testing and Materials. (2008). Standard test methods for sodium carboxymethylcellulose. ASTM D1439-03(2008)e1. ASTM International, West Conshohocken, PA, doi:10.1520/D1439-03R08E01.
3. Baumann H., Richter A., Klemm D., and Faust V. Concepts for preparation of novel regioselective modified cellulose derivatives sulphated, aminated, carboxylated and acetylated for homocompatible ultrathin coating on biomaterials. Macromolecular Chemistry and Physics 201 (2000) 1950-1962
4. Besemer A.C., de Nooy A.E.J., and van Bekkum H. Methods for the selective oxidation of cellulose: Preparation of 2,3-dicarboxycellulose and 6-carboxycellulose. In: Heinze T., and Glasser W.G. (Eds). Cellulose derivatives: Modification, characterization, and nanostructures: ACS Symposium Series 688 (1998), American Chemical Society, Washington, DC 73-82
5. Bourin M.C., and Lindahl U. Glycosaminoglycans and the regulation of blood coagulation. Biochemical Journal 289 (1993) 313-330
6. Capila I., and Linhardt R.J. Heparin-Protein Wechselwirkungen. Angewandte Chemie 114 (2002) 426-450
7. Carroll L.A., and Koch R.J. Heparin stimulates production of bFGF and TGF-beta 1 by human normal, keloid, and fetal dermal fibroblasts. Medical Science Monitor 9 3 (2003) BR97-BR108
8. Chang P.S., and Robyt J.F. Oxidation of primary alcohol groups of naturally occurring polysaccharides with 2,2,6,6-tetramethyl-1-piperidine oxoammonium ion. Journal of Carbohydrate Chemistry 15 7 (1996) 819-830
9. Da Silva Perez D., Montanari S., and Vignon M.R. TEMPO-mediated oxidation of cellulose III. Biomacromolecules 4 (2003) 1417-1425
10. Darnell J., Lodish H., and Baltimore D. Molecular cell biology. 2nd edition (1990), De Gruyter, New York
11. De Nooy A.E.J., Besemer A.C., Van Bekkum H., Van Dijk J.A.P.P., and Smit J.A.M. TEMPO-mediated oxidation of pullulan and influence of ionic strength and linear charge density on the dimensions of the obtained polyelectrolyte chains. Macromolecules 29 (1996) 6541-6547
12. Fischer S., Thümmler K., Volkert B., Hettrich K., Schmidt I., and Fischer K. Properties and applications of cellulose acetate. Macromolecular Symposia 262 (2008) 89-96
13. Gericke M., Liebert T., and Heinze T. Interaction of ionic liquids with polysaccharides, 8 - Synthesis of cellulose sulphates suitable for polyelectrolyte complex formation. Macromolecular Bioscience 9 (2009) 343-353
14. Groth T., and Wagenknecht W. Anticoagulant potential of regioselective derivatized cellulose. Biomaterials 22 (2001) 2719-2729
15. Hatanaka K., Ohtsuki T., and Kunou M. Effects of synthetic polyanions on 3T3-L1 fibroblast proliferation stimulated by fibroblast growth factors. Chemical Letters 8 (1994) 1407-1410
16. Heinze T., and Koschella A. Carboxymethyl ethers of cellulose and starch - a review. Macromolecular Symposia 223 (2005) 13-29
17. Hettrich K., Wagenknecht W., Volkert B., and Fischer S. New possibilities of the acetosulfation of cellulose. Macromolecular Symposia 262 (2008) 162-169
18. Isogai A., and Kato Y. Preparation of polyuronic acid from cellulose by TEMPO-mediated oxidation. Cellulose 5 (1998) 153-164
19. Isogai T., Yanagisawa M., and Isogai A. Degrees of polymerization (DP) and DP distribution of cellouronic acids prepared from alkali-treated celluloses and ball-milled native celluloses by TEMPO-mediated oxidation. Cellulose 16 (2009) 117-127
20. Kato Y., Matsuo R., and Isogai A. Oxidation process of water-soluble starch in TEMPO-mediated system. Carbohydrate Polymers 51 (2003) 69-75
21. Kunou M., and Hatanaka K. Effects of heparin, dextran sulphate, and synthetic (16)-α-D-mannopyranan sulphate and acidic fibroblast growth factor on 3T3-L1 fibroblasts. Carbohydrate Polymers 28 (1995) 107-112
22. Kunou M., Koizumi M., Shimizu K., Kawase M., and Hatanaka K. Synthesis of sulphated colominic acids and their interaction with fibroblast growth factors. Biomacromolecules 1 (2000) 451-458
23. Leali D., Belleri M., Urbinati C., Coltrini D., Oreste P., Zoppetti G., et al. Fibroblast growth factor-2 antagonist activity and angiostatic capacity of sulphated Escherichia coli K5 polysaccharide derivatives. The Journal of Biological Chemistry 276 (2001) 37900-37908
24. Liekens S., Leali D., Neyts J., Esnouf R., Rusnati M., Dell'Era P., et al. Modulation of fibroblast growth factor-2 receptor binding, signaling, and mitogenic activity by heparin-mimicking polysulfonated compounds. Molecular Pharmacology 56 (1999) 204-213
25. Montanari S., Roumani M., Heux L., and Vignon M.R. Topochemistry of carboxylated cellulose nanocrystals resulting from TEMPO-mediated oxidation. Macromolecules 38 (2005) 1665-1671
26. Mulloy B., Mourão P.A.S., and Gray E. Structure/function studies of anticoagulant sulphated polysaccharides using NMR. Journal of Biotechnology 77 (2000) 123-135
27. 13C-NMR spectroscopy. Progress in Polymer Science 19 (1994) 29-78
28. Peschel, D., Zhang, K., Aggarwal, N., Brendler, E., Fischer, S., & Groth, T. (in press). Synthesis of novel celluloses derivatives and investigation of their mitogenic activity in the presence and absence of FGF2. Acta Biomaterialia, doi:10.1016/j.actbio.2009.12.032.
29. 4-DMF system. Carbohydrate Research 164 (1987) 107-116
30. Philipp B., and Wagenknecht W. Cellulose sulphate half-ester. Synthesis, structure and properties. Cellulose Chemistry & Technology 17 (1983) 443-459
31. Rabenstein D.L. Heparin and heparin sulphate: Structure and function. Natural Product Reports 19 (2002) 312-331
32. Saito T., and Isogai A. TEMPO-mediated oxidation of native cellulose. The effect of oxidation conditions on chemical and crystal structures of the water-insoluble fractions. Biomacromolecules 5 (2004) 1983-1989
33. Saito T., and Isogai A. Ion-exchange behaviour of carboxylate groups in fibrous cellulose oxidized by the TEMPO-mediated system. Carbohydrate Polymers 61 (2005) 183-190
34. Saito T., Kimura S., Nishiyama Y., and Isogai A. Cellulose nanofibers prepared by TEMPO-mediated oxidation of native cellulose. Biomacromolecules 8 (2007) 2485-2491
35. Saito T., Yanagisawa M., and Isogai A. TEMPO-mediated oxidation of native cellulose: SEC-MALLS analysis of water-soluble and-insoluble fractions in the oxidized products. Cellulose 12 (2005) 305-315
36. Shibata I., and Isogai A. Depolymerisation of cellouronic acid during TEMPO-mediated oxidation. Cellulose 10 (2003) 151-158
37. Shibata I., Yanagisawa M., and Isogai A. SEC-MALLS analysis of cellouronic acid prepared from regenerated cellulose by TEMPO-mediated oxidation. Cellulose 12 (2006) 305-315
38. Socrates G. Infrared and Raman characteristic group frequencies. 3rd edition (2001), John Wiley & Sons Ltd, England
39. Tahiri C., and Vignon M.R. TEMPO-oxidation of cellulose: synthesis and characterisation of polyglucuronans. Cellulose 7 (2000) 177-188
40. Wang Z.M., Li L., Xiao K.J., and Wu J.Y. Homogeneous sulfation of bagasse cellulose in an ionic liquid and anticoagulant activity. Bioresource Technology 100 (2009) 1687-1690
41. Wang Z.M., Li L., Zheng B.S., Normakhamatov N., and Guo S.Y. Preparation and anticoagulation activity of sodium cellulose sulphate. International Journal of Biological Macromolecules 41 (2007) 376-382
42. Xing R., Liu S., Yu H., Zhang Q., Li Z., and Li P. Preparation of low-molecular-weight and high-sulphate-content chitosans under microwave radiation and their potential antioxidant activity in vitro. Carbohydrate Polymers 339 (2004) 2515-2519
43. Yamamoto I., Takayama K., Matsuzaki K., Hatanaka K., Uryu T., Yamamoto N., et al. Synthesis, structure and antiviral activity of sulphates of cellulose and its branched derivatives. Carbohydrate Polymers 14 (1991) 53-63
44. Zhang K., Brendler E., and Fischer S. FT Raman investigation of sodium cellulose sulfate. Cellulose 17 (2010) 427-435
45. Zhang K., Peschel D., Brendler E., Groth T., and Fischer S. Bioactivity of cellulose derivatives. Macromolecular Symposia 280 (2009) 28-35
46. Zhou H., Qian J., Wang J., Yao W., Liu C., Chen J., et al. Enhanced bioactivity of bone morphogenetic protein-2 with low dose of 2-N, 6-O-sulfated chitosan in vitro and in vivo. Biomaterials 30 (2009) 1715-1724