Preparation of completely C6-carboxylated curdlan by catalytic oxidation with 4-acetamido-TEMPO

Carbohydrate Polymers

Volumn 100, Issue , 2014, Pages 74-79

  Watanabe, Erika ^a   Tamura, Naoyuki ^a   Saito, Tsuguyuki ^a   Habu, Naoto ^b   Isogai, Akira ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b UTSUNOMIYA UNIVERSITY   (Japan)

Author keywords

(1 3) Polyglucuronic acid; 4 Acetamido TEMPO; Curdlan; Molecular weight; Oxidation

Indexed keywords

4 ACETAMIDO TEMPOS; CURDLAN; DEGREES OF POLYMERIZATIONS; HIGH MOLECULAR WEIGHT; NMR CHEMICAL SHIFTS; OXIDATION CONDITIONS; POLYGLUCURONIC ACID; TWO-STEP REACTIONS; OXIDATION PROCESS;

CARBOXYLATION; CATALYTIC OXIDATION; MOLECULAR WEIGHT; OXIDATION; TRANSPORT PROPERTIES; CHEMICAL REACTIONS; FOOD ADDITIVES;

FOOD ADDITIVES; CATALYTIC OXIDATION;

AMINE OXIDE; BETA GLUCAN; CARBOXYLIC ACID; CHLORIDE; CHLORITE; CURDLAN; GLUCURONIC ACID; HYPOCHLORITE SODIUM; TEMPO;

(1→3)-Β-POLYGLUCURONIC ACID; 4-ACETAMIDO-TEMPO; ARTICLE; CATALYSIS; CHEMISTRY; MOLECULAR WEIGHT; OXIDATION; OXIDATION REDUCTION REACTION; POLYMERIZATION;

(1→3)-Β-POLYGLUCURONIC ACID; 4-ACETAMIDO-TEMPO; CURDLAN; MOLECULAR WEIGHT; OXIDATION;

BETA-GLUCANS; CARBOXYLIC ACIDS; CATALYSIS; CHLORIDES; CYCLIC N-OXIDES; GLUCURONIC ACID; OXIDATION-REDUCTION; POLYMERIZATION; SODIUM HYPOCHLORITE;

EID: 84887457623     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2012.11.094     Document Type: Article

References (24)

1. ASTRA for Windows user's guide version 4.90.
2. J.A. Bohn, and J.N. BeMiller (1→3)-β-d-glucans as biological response modifiers: A review of structure-functional activity relationships Carbohydrate Polymers 28 1995 3 14
3. P.L. Bragd, A.C. Besemer, and H. van Bekkum TEMPO-derivatives as catalysts in the oxidation of primary alcohol groups in carbohydrates Journal of Molecular Catalysis A: Chemical 170 2001 35 42 (Pubitemid 32405637)
4. C.T. Chuah, A. Sarko, Y. Deslandes, and R.H. Marchessault Packing analysis of carbohydrates and polysaccharides. Part 14. Triple-helical crystalline structure of curdlan and paramylon hydrates Macromolecules 16 1983 1375 1382
5. A.E.J. de Nooy, A.C. Besemer, and H. van Bekkum Highly selective nitroxyl radical-mediated oxidation of primary alcohol groups in water-soluble glucans Carbohydrate Research 269 1995 89 98
6. Y. Deslandes, R.H. Marchessault, and A. Sarko Triple-helical structure of (1→3)-β-d-glucan Macromolecules 13 1980 1466 1471
7. J. Duan, and D.L. Kasper Oxidative depolymerization of polysaccharides by reactive oxygen/nitrogen species Glycobiology 21 2010 401 409
8. T. Harada, A. Misaki, and H. Saito Curdlan: A bacterial gel-forming β-1,3-glucan Archives of Biochemistry and Biophysics 124 1968 292 298
9. A. Isogai, and Y. Kato Preparation of polyuronic acid from cellulose by TEMPO-mediated oxidation Cellulose 5 1998 153 164 (Pubitemid 128514301)
10. T. Isogai, M. Yanagisawa, and A. Isogai 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
11. A. Kantouch, A. Hebeish, and M.H. El-Rafie Action of sodium chloride on cellulose and cellulose derivatives Textile Research Journal 40 1970 178 184
12. K. Kataoka, T. Muta, S. Yamazaki, and K. Takeshige Activation of macrophages by linear (1→3)-β-d-glucans - Implications for the recognition of fungi by innate immunity The Journal of Biological Chemistry 277 2002 36825 36831
13. Y. Kato, J. Kaminaga, R. Matsuo, and A. Isogai TEMPO-mediated oxidation of chitin, regenerated chitin and N-acetylated chitosan Carbohydrate Polymers 58 2004 421 426
14. Y. Kato, R. Matsuo, and A. Isogai Oxidation process of water-soluble starch in TEMPO-mediated system Carbohydrate Polymers 51 2003 69 75
15. M. McIntosh, B.A. Stone, and V.A. Stanisich Curdlan and other bacterial (1→3)-β-d-glucans Applied Microbiology and Biotechnology 68 2005 163 173
16. T.N.L. Le, T. Shiraki, A. Dawn, Y. Tsuchiya, D. Tokunaga, and S. Tamaru A pH-responsive carboxylic beta-1,3-glucan polysaccharide for complexation with polymeric guests Organic & Biomolecular Chemistry 9 2011 4266 4275
17. M. Lewin Oxidation and aging of cellulose Macromolecular Symposia 118 1997 715724
18. S. Li, Y. Zhang, X. Xu, and L. Zhang Triple helical polysaccharide- induced good dispersion of silver nanoparticles in water Biomacromolecules 12 2011 2864 2871
19. R.A.A. Muzzarelli, C. Muzzarelli, A. Cosani, and M. Terbojevich 6-Oxychitins, novel hyaluronan-like regiospecifically carboxylated chitins Carbohydrate Polymers 39 1999 361 367
20. V.E.C. Ooi, and F. Liu Immunomodulation and anti-cancer activity of polysaccharide-protein complexes Current Medicinal Chemistry 7 2000 715 729 (Pubitemid 30366638)
21. V.A. Shenai, and A.G. Date Studies in chemically modified celluloses. IX. Oxidation of cellulose in the presence of chelating agents Journal of Applied Polymer Science 20 1976 385 391
22. 2 under acid conditions Carbohydrate Polymers 81 2010 592 598
23. N. Tamura, M. Wada, and A. Isogai TEMPO-mediated oxidation of (1→3)-β-d-glucans Carbohydrate Polymers 77 2009 300 305
24. T. Toida, A. Chaidedgumjorn, and R.J. Linhardt Structure and bioactivity of sulfated polysaccharides Trends Glycoscience Glycotechnology 15 2003 29 37