Highly C6-selective and quantitative modification of cellulose: Nucleoside-appended celluloses to solubilize single walled carbon nanotubes

Cellulose

Volumn 18, Issue 1, 2011, Pages 83-93

  Kawagoe, Natsumi ^a   Kasori, Yuki ^a   Hasegawa, Teruaki ^a  

^a TOYO UNIVERSITY   (Japan)

Author keywords

Artificial DNA; Azidation; Bromination; Cellulose; Click chemistry; Direct modification; Regioselective modification; Single walled carbon nanotubes

Indexed keywords

CELLULOSE; CELLULOSE DERIVATIVES; NANOTUBES;

AZIDATION; BROMINATION; CLICK CHEMISTRY; DIRECT MODIFICATION; REGIOSELECTIVE MODIFICATION;

SINGLE-WALLED CARBON NANOTUBES (SWCN);

CATALYSTS; CELLULOSE DERIVATIVES; NUCLEIC ACIDS; PAPER SHEETS;

EID: 79251594636     PISSN: 09690239     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10570-010-9468-9     Document Type: Article

References (28)

1. Atkins EDT, Parker KD (1968) Cyclic triad of hydrogen bonds in a helical polymer. Nature 220: 784-785. doi: 10. 1038/220784a0.
2. Deslandes Y, Marchessault RH, Sarko A (1980) Triple-helical structure of (1 - > 3)- β-D-glucans. Macromolecules 13: 1466-1471.
3. Furuhata K, Aoki N, Suzuki S, Sakamoto M, Saegusa Y, Nakamura S (1995) Bromination of cellulose with tribromoimidazole, triphenylphosphine and imidazole under homogeneous conditions in lithium bromide-dimethylacetamide. Carbohydr Polym 26: 25-29.
4. Hasegawa T, Umeda M, Numata M, Li C, Bae AH, Fujisawa T, Haraguchi S, Sakurai K, Shinkai S (2006a) 'Click chemistry' on polysaccharides: a convenient, general, and monitorable approach to develop (1 - > 3)-β-D-glucans with various functional appendages. Carbohydr Res 341: 35-40. doi: 10. 1016/j. carres. 2005. 10. 009.
5. Hasegawa T, Umeda M, Numata M, Fujisawa T, Haraguchi S, Sakurai K, Shinkai S (2006b) Click chemistry on curdlan: a regioselective and quantitative approach to develop artificial β-1, 3-glucans with various functional appendages. Chem Lett 35: 82-83. doi: 10. 1246/cl. 2006. 82.
6. Hasegawa T, Numata M, Okumura S, Kimura T, Sakurai K, Shinkai S (2007) Carbohydrate-appended curdlans as a new family of glycoclusters with binding properties both for a polynucleotide and lectins. Org Biomol Chem 5: 2404-2412. doi: 10. 1039/b703720a.
7. Ikai T, Yamamoto C, Kamigaito M, Okamoto Y (2008) Organic-inorganic hybrid materials for efficient enantioseparation using cellulose 3, 5-dimethylphenylcarbamate and tetraethyl orthosilicate. Chem -Asian J 3: 1494-1499. doi: 10. 1002/asia. 200800022.
8. Jahn M, Stoll D, Warren RAJ, Szabo L, Singh P, Gilbert HJ, Ducros VMA, Davies GJ, Withers SG (2003) Expansion of the glycosynthase repertoire to produce defined manno-oligosaccharides. Chem Commun 1327-1329. doi: 10. 1039/b302380j.
9. Ke G (2009) Homogeneous modification of carbon nanotubes with cellulose acetate. Chin Chem Lett 20: 1376-1380. doi: 10. 1016/j. cclet. 2009. 07. 021.
10. Ke G, Guan WC, Tang CY, Hu Z, Guan WJ, Zeng DL, Deng F (2007) Covalent modification of multiwalled carbon nanotubes with a low molecular weight chitosan. Chin Chem Lett 18: 361-364. doi: 10. 1016/j. cclet. 2007. 01. 010.
11. Kobayashi S, Uyama H, Kimura S (2001) Enzymatic polymerization. Chem Rev 101: 3793-3818. doi: 10. 1021/cr990121l.
12. Li WY, Jin AX, Liu CF, Sun RC, Zhang AP, Kennedy JF (2009) Homogeneous modification of cellulose with succinic anhydride in ionic liquid using 4-dimethylaminopyridine as a catalyst. Carbohydr Polym 78: 389-395. doi: 10. 1016/j. carbpol. 2009. 04. 028.
13. Lii CY, Stobinski L, Tomasik P, Liao CD (2003) Single-walled carbon nanotube-potato amylose complex. Carbohydr Polym 51: 93-98.
14. Manohar S, Mantz AR, Bancroft KE, Hui CY, Jagota A, Vezenov DV (2008) Peeling Single-Stranded DNA from Graphite Surface to Determine Oligonucleotide Binding Energy by Force Spectroscopy. Nano Lett. 8: 4365-4372. doi: 10. 1021/nl8022143.
15. Mocharla VP, Colasson B, Lee LV, Roper S, Sharpless KB, Wong CH, Kolb HC (2005) In situ click chemistry: Enzyme-generated inhibitors of carbonic anhydrase II. Angew Chem Int Edit 44: 116-120. doi: 10. 1002/anie. 200461580.
16. Numata M, Asai M, Kaneko K, Bae AH, Hasegawa T, Sakurai K, Shinkai S (2005) Inclusion of cut and as-grown single-walled carbon nanotubes in the helical superstructure of schizophyllan and curdlan (ss-1, 3-glucans). J Am Chem Soc 127: 5875-5884. doi: 10. 1021/ja044168m.
17. Okamoto E, Kiyosada T, Shoda SI, Kobayashi S (1997) Synthesis of alternatingly 6-O-methylated cellulose via enzymatic polymerization of a substituted cellobiosyl fluoride monomer catalyzed by cellulase. Cellulose 4: 161-172.
18. Qian XH (2008) The effect of cooperativity on hydrogen bonding interactions in native cellulose Iβ from ab initio molecular dynamics simulations. Mol Simulat 34: 183-191. doi: 10. 1080/08927020801961476.
19. Roy D, Semsarilar M, Guthrie JT, Perrier S (2009) Cellulose modification by polymer grafting: a review. Chem Soc Rev 38: 2046-2064. doi: 10. 1039/b808639g.
20. Sakurai K, Shinkai S (2000) Molecular recognition of adenine, cytosine, and uracil in a single-stranded RNA by a natural polysaccharide: Schizophyllan. J Am Chem Soc 122: 4520-4521.
21. Sakurai K, Uezu K, Numata M, Hasegawa T, Li C, Kaneko K, Shinkai S (2005) β-1, 3-Glucan polysaccharides as novel one-dimensional hosts for DNA/RNA, conjugated polymers and nanoparticles. Chem Commun 4383-4398. doi: 10. 1039/b506673p.
22. Star A, Steuerman DW, Heath JR, Stoddart JF (2002) Starched carbon nanotubes. Angew Chem Int Ed 14: 2508-2512.
23. Sugiura Y, Yamamoto C, Ikai T, Kamigaito M, Okamoto Y (2010) Enantioseparation using amylose esters as chiral stationary phases for high-performance liquid chromatography. Polym J 42: 31-36. doi: 10. 1038/pj. 2009. 300.
24. Tornøe CW, Christensen C, Meldal M (2002) Peptidotriazoles on solid phase: 1, 2, 3 -triazoles by regiospecific copper(I)-catalyzed 1, 3-dipolar cycloadditions of terminal alkynes to azides. J Org Chem 67: 3057-3064. doi: 10. 1021/jo011148j.
25. Watson RM, Skorik YA, Patra GK, Achim C (2005) Influence of metal coordination on the mismatch tolerance of ligand-modified PNA duplexes. J Am Chem Soc 127: 14628-14639. doi: 10. 1021/ja051336h.
26. Yamashita E, Okubo K, Negishi K, Hasegawa T (2009) Regioselective and quantitative modification of cellulose to access cellulose-based advanced materials: cellulose-based glycoclusters. Chem Lett 38: 122-123. doi: 10. 1246/cl. 2009. 122.
27. Yang Q, Pan XJ (2010) Preparation and characterization of water-soluble single-walled carbon nanotubes by hybridization with hydroxypropyl cellulose derivatives. Ind Eng Chem Res 49: 2747-2751. doi: 10. 1021/ie9014149.
28. Zheng M, Jagota A, Semke ED, Diner BA, McLean RS, Lustig SR, Richardson RE, Tassi NG (2003) DNA-assisted dispersion and separation of carbon nanotubes. Nat Mater 2: 338-342. doi: 10. 1038/nmat877.