Preparation of highly regioselective chitosan derivatives via "click chemistry"

Carbohydrate Polymers

Volumn 85, Issue 3, 2011, Pages 653-657

  Ifuku, Shinsuke ^a   Wada, Masahiro ^a   Morimoto, Minoru ^a   Saimoto, Hiroyuki ^a  

^a TOTTORI UNIVERSITY   (Japan)

Author keywords

Chitosan; Click chemistry; Huisgen cycloaddition; Regioselective modification

Indexed keywords

AZIDATION; CHITOSAN DERIVATIVES; CLICK CHEMISTRY; COPPER (II); ELEMENTAL ANALYSIS; ETHYNYL; FTIR; HUISGEN CYCLOADDITION; NMR SPECTRUM; PHENYL GROUP; REGIO-SELECTIVE; REGIOSELECTIVE BROMINATION; REGIOSELECTIVE MODIFICATION; SODIUM ASCORBATE; TRIETHYLAMINES;

CHITOSAN; COMPLEXATION; CYCLOADDITION; FUNCTIONAL GROUPS; METHANOL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REGIOSELECTIVITY; SODIUM; SODIUM SULFATE;

CHITIN;

EID: 79955669249     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2011.03.030     Document Type: Article

References (15)

1. H. Bao, L. Li, L.H. Gan, Y. Ping, L. Li, and P. Ravi Thermo- and pH-responsive association behavior of dual hydrophilic graft chitosan terpolymer synthesized via ATRP and click chemistry Macromolecules 43 2010 5679 5687
2. K. Furuhata, H. Chang, N. Aoki, and M. Sakamoto Chlorination of cellulose with N-chlorosuccinimide-triphenylphosphine under homogeneous conditions in lithium chloride-N,N-dimethylacetamide Carbohydrate Research 230 1992 151 164
3. Y. Gao, Z. Zhang, L. Chen, W. Gu, and Y. Li Synthesis of 6-N,N,N-trimethyltriazole chitosan via "click chemistry" and evaluation for gene delivery Biomacromolecules 10 2009 2175 2182
4. T. Hasegawa, M. Umeda, M. Numata, C. Li, A.H. Bae, and T. Fujisawa 'Click chemistry' on polysaccharides: A convenient, general, and monitorable approach to develop (1 → 3)-β-d-glucans with various functional appendages Carbohydrate Research 341 2006 35 40 (Pubitemid 41796974)
5. H.C. Kolb, M.G. Finn, and K.B. Sharpless Click chemistry: Diverse chemical function from a few good reactions Angewandte Chemie International Edition 40 2001 2004 2021
6. R. Kulbokaite, G. Ciuta, M. Netopilik, and R. Makuska N-PEG'ylation of chitosan via "click chemistry" reactions Reactive & Functional Polymers 69 2009 771 778
7. K. Kurita Controlled functionalization of the polysaccharide chitin Progress in Polymer Science 26 2001 1921 1971 (Pubitemid 33089088)
8. K. Kurita, H. Ikeda, Y. Yoshida, M. Shimojoh, and M. Harata Chemoselective protection of the amino groups of chitosan by controlled phthaloylation: Facile preparation of a precursor useful for chemical modifications Biomacromolecules 3 2002 1 4 (Pubitemid 34121151)
9. L.V. Lee, M.L. Mitchel, S.-J. Huang, V.V. Fokin, K.B. Sharpless, and C.-H. Wong A potent and highly selective inhibitor of human α-1,3- fucosyltransferase via click chemistry Journal of the American Chemical Society 125 2003 9588 9589 (Pubitemid 36975912)
10. T. Liebert, C. Hänsch, and T. Heinze Click chemistry with polysaccharide Macromolecular Rapid Communications 27 2006 208 213
11. R. Manetsch, A. Krasiński, A. Radić, J. Raushel, P. Taylor, and K.B. Sharpless In situ click chemistry: Enzyme inhibitors made to their own specifications Journal of the American Chemical Society 126 2004 12809 12818 (Pubitemid 39372310)
12. V.V. Rostovtsev, L.G. Green, V.V. Fokin, and K.B. Sharpless A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes Angewandte Chemie International Edition 114 2002 2708 2711
13. T. Satoh, H. Kano, M. Nakatani, N. Sakairi, S. Shinkai, and T. Nagasaki 6-Amino-6-deoxy-chitosan. sequential chemical modifications at the C-6 positions of N-phthaloyl-chitosan and evaluation as a gene carrier Carbohydrate Research 341 2006 2406 2413 (Pubitemid 44279604)
14. P. Wu, A.K. Feldman, A.K. Nugent, C.J. Hawker, A. Scheel, and B. Voit Efficiency and fidelity in a click-chemistry route to triazole dendrimers by the copper(I)-catalyzed ligation of azides and alkynes Angewandte Chemie International Edition 43 2004 3928 3932 (Pubitemid 39257472)
15. G. Zampano, M. Bertoldo, and F. Ciardelli Defined chitosan-based networks byC-6-azide-alkyne "click" reaction Reactive & Functional Polymers 70 2010 272 281