2-Azido-2-deoxycellulose: Synthesis and 1,3-dipolar cycloaddition

Helvetica Chimica Acta

Volumn 91, Issue 4, 2008, Pages 608-617

  Zhang, Fuyi ^a   Bernet, Bruno ^a   Bonnet, Véronique ^a   Dangles, Olivier ^a   Sarabia, Francisco ^a   Vasella, Andrea ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

AVERAGE MOLECULAR; BASIC HYDROLYSIS; DEACETYLATION; DIAZO TRANSFERS; DIPOLAR CYCLOADDITION; HIGH YIELDS; PHTHALOYLCHITOSAN;

ACETYLENE; CHITIN; CHITOSAN; CYCLOADDITION; DIMETHYL SULFOXIDE; HYDROCARBONS; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

AMINES;

2 (4 BENZYL 1H 1,2,3 TRIAZOL 1 YL) 2 DEOXYCELLULOSE; 2 (4 BUTYL 1H 1,2,3 TRIAZOL 1 YL) 2 DEOXYCELLULOSE; 2 AZIDO 2 DEOXY 3,6 DI O FORMYLCELLULOSE; 2 AZIDO 2 DEOXY 6 O (TRIPHENYLMETHYL)CELLULOSE; 2 AZIDO 2 DEOXY 6 O [(4 METHOXYPHENYL)DIPHENYLMETHYL]CELLULOSE; 2 AZIDO 2 DEOXYCELLULOSE; 2 CEOXY 2 [4 (3 PHENYLPROPYL) 1H 1,2,3 TRIAZOL 1 YL]CELLULOSE; 2 DEOXY 2 (4 HEXYL 1H 1,2,3 TRIAZOL 1 YL)CELLULOSE; 2 DEOXY 2 (4 PENTYL 1H 1,2,3 TRIAZOL 1 YL)CELLULOSE; 2 DEOXY 2 (4 PHENYL 1H 1,2,3 TRIAZOL 1 YL)CELLULOSE; 2 DEOXY 2 [4 (2 PHENYLETHYL) 1H 1,2,3 TRIAZOL 1 YL]CELLULOSE; 6 O (TRIPHENYLMETHYL)CHITOSAN; 6 O [(4 METHOXYPHENYL)DIPHENYLMETHYL] N PHTHALOYLCHITOSAN; 6 O [(4 METHOXYPHENYL)DIPHENYLMETHYL]CHITOSAN; CELLULOSE DERIVATIVE; CHITOSAN DERIVATIVE; N PHTHALOYL 6 O (TRIPHENYLMETHYL)CHITOSAN; N PHTHALOYLCHITOSAN; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLOADDITION; DEACETYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 55249105138     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200890064     Document Type: Article

References (129)

1. R. A. A. Muzzarelli, 'Chitin', Pergamon Press, Oxford, UK, 1977;
2. G. A. F. Roberts, 'Chitin Chemistry', Macmillan, Basingstoke, Hampshire, 1992;
3. P. Jollès, R. A. A. Muzzarelli, 'Chitin and Chitinases', Birkhäuser, Basel, 1999, p. 340;
4. M. G. Peter, in 'Biopolymers: Biology, Chemistry, Biotechnology, Applications. Vol. 6. Polysaccharides II: Polysaccharides from Eukaryotes', Eds. E. J. Vandamme, S. De Baets, A. Steinbüchel, Wiley-VCH, Weinheim, 2002, p. 481-574;
5. 'Special Issue: Chitin and Chitosan', Macromol. Biosci. 2003, 3, 503.
6. J. Ferrer, G. Paez, Z. Marmol, E. Ramones, H. Garcia, C. F. Forster, Bioresour. Technol. 1996, 57, 55;
7. J. Synowiecki, N. A. Al-Khateeb, Crit. Rev. Food Sci. Nutr. 2003, 43, 145.
8. D. J. Macquarrie, J. J. E. Hardy, Ind. Eng. Chem. Res. 2005, 44, 8499;
9. P. K. Dutta, J. Dutta, V. S. Tripathi, J. Sci. Ind. Res. 2004, 63, 20;
10. P. K. Dutta, M. N. Ravikumar, J. Dutta, J. Macromol. Sci., Part C: Polym. Rev. 2002, 42, 307;
11. M. N. V. R. Kumar, R. A. A. Muzzarelli, C. Muzzarelli, H. Sashiwa, A. J. Domb, Chem. Rev. 2004, 104, 6017;
12. M. N. V. R. Kumar, React. Funct. Polym. 2000, 46, 1;
13. M. Morimoto, H. Saimoto, Y. Shigemasa, Trends Glycosci. Glycotechnol. 2002, 14, 205;
14. M. H. Struszczyk, Polymery 2002, 47, 316;
15. M. H. Struszczyk, Polymery 2002, 47, 396;
16. Q. Li, E. W. Grandmaison, M. F. A. Goosen, E. T. Dunn, J. Bioact. Compat. Polym. 1992, 7, 370;
17. M. Rinaudo, Prog. Polym. Sci. 2006, 31, 603;
18. E. Ruel-Gariepy, J.-C. Leroux, Polysaccharides Drug Delivery Pharm. Appl. 2006, 934, 243.
19. E. I. Rabea, M. E. T. Badawy, C. V. Stevens, G. Smagghe, W. Steurbaut, Biomacromolecules 2003, 4, 1457;
20. S. H. Lim, S. M. Hudson, J. Macromol. Sci., Part C: Polym. Rev. 2003, 43, 223;
21. S. N. Chirkov, Appl. Biochem. Microbiol. 2002, 38, 1.
22. B. Krajewska, Enzyme Microb. Technol. 2004, 35, 126;
23. A. Bernkop-Schnürch, C. E. Kast, Adv. Drug Delivery Rev. 2001, 52, 127.
24. R. Jayakumar, M. Prabaharan, R. L. Reis, J. F. Mano, Carbohydr. Polym. 2005, 62, 142;
25. D. W. Jenkins, S. M. Hudson, Chem. Rev. 2001, 101, 3245.
26. M. Prabaharan, J. F. Mano, Drug Delivery 2005, 12, 41;
27. V. R. Sinha, A. K. Singla, S. Wadhawan, R. Kaushik, R. Kumria, K. Bansal, S. Dhawan, Int. J. Pharm. 2004, 274, 1;
28. S. A. Agnihotri, N. N. Mallikarjuna, T. M. Aminabhavi, J. Controlled Release 2004, 100, 5;
29. P. K. Dutta, M. K. Khatua, J. Dutta, R. Prasad, Int. J. Chem. Sci. 2003, 1, 93;
30. V. Dodane, V. D. Vilivalam, Pharm. Sci. Technol. Today 1998, 1, 246;
31. O. Felt, P. Buri, R. Gurny, Drug Dev. Ind. Pharm. 1998, 24, 979;
32. H. S. Kas, J. Microencapsulation 1997, 14, 689.
33. T.-H. Kim, H.-L. Jiang, D. Jere, I.-K. Park, M.-H. Cho, J.-W. Nah, Y.-J. Choi, T. Akaike, C.-S. Cho, Prog. Polym. Sci. 2007, 32, 726;
34. K. Y. Lee, Macromol. Res. 2007, 15, 195;
35. G. Borchard, Adv. Drug Delivery Rev. 2001, 52, 145.
36. R. A. A. Muzzarelli, C. Muzzarelli, in 'Advances in Polymer Chemistry 186: Polysaccharide I: Structure, Characterization and Use', Ed. T. Heinze, Springer-Verlag, 2005, p. 151-209;
37. A. Di Martino, M. Sittinger, M. V. Risbud, Biomaterials 2005, 26, 5983;
38. M. Ishihara, Trends Glycosci. Glycotechnol. 2002, 78, 331;
39. A. K. Singla, M. Chawla, J. Pharm. Pharmacol. 2001, 53, 1047;
40. H. Ueno, T. Mori, T. Fujinaga, Adv. Drug Delivery Rev. 2001, 52, 105;
41. D. K. Singh, A. R. Ray, J. Macromol. Sci., Part C: Polym. Rev. 2000, 40, 69;
42. J. K. F. Suh, H. W. T. Matthew, Biomaterials 2000, 21, 2589;
43. O. Skaugrud, A. Hagen, B. Borgersen, M. Dornish, Biotechnol. Genet. Eng. Rev. 1999, 16, 23;
44. Y. Shigemasa, S. Minami, Biotechnol. Genet. Eng. Rev. 1996, 13, 383.
45. H. K. No, S. P. Meyers, W. Prinyawiwatkul, Z. Xu, J. Food Sci. 2007, 72, R87;
46. F. Shahidi, J. K. V. Arachchi, Y. J. Jeon, Trends Food Sci. Technol. 1999, 10, 37;
47. S. S. Koide, Nutr. Res. 1998, 18, 1091.
48. R.-M. Wang, X. Xie, J.-Q. Wang, S.-J. Pan, Y.-P. Wang, C.-G. Xia, Polym. Adv. Technol. 2004, 15, 52;
49. E. Guibal, Sep. Purif. Technol. 2004, 38, 43;
50. A. J. Varma, S. V. Deshpande, J. F. Kennedy, Carbohydr. Polym. 2004, 55, 77;
51. G. Cardenas, P. Orlando, T. Edelio, Int. J. Biol. Macromol. 2001, 28, 167;
52. D. D. Hu, Q. Z. Shi, Z. X. Tang, Y. Fang, Chin. J. Inorg. Chem. 2000, 16, 385.
53. C. Gerente, V. K. C. Lee, C. Le, P. G. McKay, Crit. Rev. Environ. Sci. Technol. 2007, 37, 41;
54. H. K. No, S. P. Meyers, Rev. Environ. Contam. Toxicol. 2000, 163, 1.
55. D. J. Macquarrie, J. J. E. Hardy, S. Hubert, A. J. Deveaux, M. Bandini, R. L. Alvarez, M. Chabrel, in 'ACS Symposium Series 921: Feedstocks for the Future: Renewables for the Production of Chemicals and Materials', Eds. J. Scheirs, W. Kaminsky, John Wiley & Sons, Hoboken, 2006, p. 170-183;
56. E. Guibal, Prog. Polym. Sci. 2005, 30, 71.
57. P. C. Srinivasa, R. N. Tharanathan, Food Rev. Int. 2007, 23, 53.
58. S.-H. Lim, S. M. Hudson, Carbohydr. Res. 2004, 339, 313;
59. Y. Kato, H. Onishi, Y. Machida, Biomaterials 2004, 25, 907;
60. H. Sashiwa, N. Yamamori, Y. Ichinose, J. Sunamoto, S. Aiba, Biomacromolecules 2003, 4, 1250;
61. J. Y. Kim, J. K. Lee, T. S. Lee, W. H. Park, Int. J. Biol. Macromol. 2003, 32, 23;
62. R. Auzély, M. Rinaudo, Macromol. Biosci. 2003, 3, 562;
63. R. A. A. Muzzarelli, F. Tanfani, M. Emanuelli, S. Mariotti, Carbohydr. Res. 1982, 107, 199;
64. K. R. Holme, L. D. Hall, Carbohydr. Res. 1992, 225, 291;
65. L. D. Hall, M. Yalpani, Macromolecules 1984, 17, 272.
66. H. Sashiwa, Y. Shigemasa, Carbohydr. Polym. 1999, 39, 127.
67. R. Jayakumar, R. L. Reis, J. F. Mano, E-Polymers 2006, 035;
68. G. L. Matevosyan, Y. S. Yukha, P. M. Zavlin, Russ. J. Gen. Chem. 2003, 73, 1725.
69. R. Jayakumar, N. Nwe, S. Tokura, H. Tamura, Int. J. Biol. Macromol. 2007, 40, 175;
70. K. R. Holme, A. S. Perlin, Carbohydr. Res. 1997, 302, 7.
71. A. Bernkop-Schnürch, M. Hornof, D. Guggi, Eur. J. Pharm. Biopharm. 2004, 57, 9.
72. T. Liebert, C. Hänsch, T. Heinze, Macromol. Rapid Commun. 2006, 27, 208.
73. L. Marmuse, S. A. Nepogodiev, R. A. Field, Org. Biomol. Chem. 2005, 3, 2225.
74. H. Baumann, C. Liu, V. Faust, Cellulose 2003, 10, 65.
75. T. Takano, J. Ishikawa, H. Kamitakahara, F. Nakatsubo, Carbohydr. Res. 2007, 342, 2456;
76. S. Zhang, T.-T. Ong, S.-C. Ng, H. S. O. Chan, Tetrahedron Lett. 2007, 48, 5487;
77. T. Heinze, A. Koschella, M. Brackhagen, J. Engelhardt, K. Nachtkamp, Macromol. Symp. 2006, 244, 74;
78. Y. Matsui, J. Ishikawa, H. Kamitakahara, T. Takano, F. Nakatsubo, Carbohydr. Res. 2005, 340, 1403;
79. S. Furubeppu, T. Kondo, A. Ishizu, Sen'i Gakkaishi 1991, 47, 592;
80. A. I. Usov, N. I. Nosova, S. I. Firgang, O. P. Golova, Vysokomol. Soedin., Ser. A 1973, 15, 1150.
81. K.-i. Furuhata, N. Arai, S. Ishizuka, H. Tseng, M. Sakamoto, SenAi Gakkaishi 1998, 54, 647.
82. T. Satoh, T. Nagasaki, N. Sakairi, S. Shinkai, Chem. Lett. 2004, 33, 340.
83. A. Vasella, C. Witzig, J.-L. Chiara, M. Martin-Lomas, Helv. Chim. Acta 1991, 74, 2073.
84. P. B. Alper, S.-C. Hung, C.-H. Wong, Tetrahedron Lett. 1996, 37, 6029.
85. K. Kurita, K. Tomita, T. Tada, S. Ishii, S.-I. Nishimura, K. Shimoda, J. Polym. Sci., Part A: Polym. Chem. 1993, 31, 485.
86. M. Lavertu, Z. Xia, A. N. Serreqi, M. Berrada, A. Rodrigues, D. Wang, M. D. Buschmann, A. Gupta, J. Pharm. Biomed. Anal. 2003, 32, 1149.
87. A. Domard, Int. J. Biol. Macromol. 1987, 9, 333;
88. H. Zhang, S. H. Neau, Biomaterials 2001, 22, 1653;
89. A. Domard, M. Rinaudo, Int. J. Biol. Macromol. 1983, 5, 49;
90. Y. Shigemasa, H. Matsuura, H. Sashiwa, H. Saimoto, Int. J. Biol. Macromol. 1996, 18, 237;
91. S. C. Tan, E. Khor, T. K. Tan, S. M. Wong, Talanta 1998, 45, 713;
92. M. L. Duarte, M. C. Ferreira, M. R. Marvao, J. Rocha, Int. J. Biol. Macromol. 2001, 28, 359;
93. S. V. Nemtsev, A. I. Gamzazade, S. V. Rogozhin, V. M. Bykova, V. P. Bykov, Appl. Biochem. Microbiol. 2002, 38, 521;
94. K. V. Harish Prashanth, F. S. Kittur, R. N. Tharanathan, Carbohydr. Polym. 2002, 50, 27;
95. X. Jiang, L. Chen, W. Zhong, Carbohydr. Polym. 2003, 54, 457;
96. P.-J. Park, J.-Y. Je, S.-K. Kim, Carbohydr. Polym. 2004, 55, 17;
97. D. H. Davies, E. R. Hayes, Methods Enzymol. 1988, 161, 442.
98. C. J. Cavender, V. J. Shiner, J. Org. Chem. 1972, 37, 3567.
99. S.-I. Nishimura, O. Kohgo, K. Kurita, H. Kuzuhara, Macromolecules 1991, 24, 4745.
100. A. Binette, J. Gagnon, Biomacromolecules 2007, 8, 1812.
101. E. Kaiser, R. L. Colescott, C. D. Bossinger, P. I. Cook, Anal. Biochem. 1970, 34, 595.
102. D. T. S. Rijkers, H. H. R. van Vugt, H. J. F. Jacobs, R. M. J. Liskamp, Tetrahedron Lett. 2002, 43, 3657.
103. P. Böhlen, S. Stein, S. Udenfriend, Arch. Biochem. Biophys. 1974, 163, 390;
104. S. Udenfriend, S. Stein, P. Böhlen, W. Dairman, W. Leimgruber, M. Weigele, Science 1972, 178, 871;
105. A. M. Felix, M. H. Jimenez, Anal. Biochem. 1973, 52, 377.
106. T. Hasegawa, M. Umeda, M. Numata, T. Fujisawa, S. Haraguchi, K. Sakurai, S. Shinkai, Chem. Lett. 2006, 35, 82;
107. T. Hasegawa, M. Umeda, M. Numata, C. Li, A.-H. Bae, T. Fujisawa, S. Haraguchi, K. Sakurai, S. Shinkai, Carbohydr. Res. 2006, 341, 35.
108. H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem., Int. Ed. 2001, 40, 2004;
109. W. G. Lewis, L. G. Green, F. Grynszpan, Z. Radić, P. R. Carlier, P. Taylor, M. G. Finn, K. B. Sharpless, Angew. Chem., Int. Ed. 2002, 41, 1053;
110. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem., Int. Ed. 2002, 41, 2596;
111. P. Wu, A. K. Feldman, A. K. Nugent, C. J. Hawker, A. Scheel, B. Voit, J. Pyun, J. M. J. Fréchet, K. B. Sharpless, V. V. Fokin, Angew. Chem., Int. Ed. 2004, 43, 3928;
112. P. Wu, V. V. Fokin, Aldrichimica Acta 2007, 40, 7.
113. C. W. Tornøe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057;
114. S. Dedola, S. A. Nepogodiev, R. A. Field, Org. Biomol. Chem. 2007, 5, 1006.
115. B. Hoffmann, B. Bernet, A. Vasella, Helv. Chim. Acta 2002, 85, 265.
116. S. Kajimo, T. Jin, Z. Huo, Y. Yamamoto, Tetrahedron Lett. 2002, 43, 9707;
117. F. Pérez-Balderas, M. Ortega-Muñoz, J. Morales-Sanfrutos, F. Hernãndez-Mateo, F. G. Calvo-Flores, J. A. Calvo-Asín, J. Isac-García, F. Santoyo-González, Org. Lett. 2003, 5, 1951.
118. H. Kono, Biopolymers 2004, 75, 255.
119. M. Fernández Cervera, J. Heinämäki, M. Räsänen, S. L. Maunu, M. Karjalainen, O. M. Nieto Acosta, A. Iraizoz Colarte, J. Yliruusi, Carbohydr. Polym. 2004, 58, 401.
120. R. H. Atalla, D. L. VanderHart, Science 1984, 223, 283;
121. D. L. VanderHart, R. H. Atalla, Macromolecules 1984, 17, 1465.
122. K. V. S. N. Murty, T. Xie, B. Bernet, A. Vasella, Helv. Chim. Acta 2006, 89, 675.
123. S. Chassaing, M. Kumarraja, A. S. S. Sido, P. Pale, J. Sommer, S. Chassaing, M. Kumarraja, A. S. S. Sido, P. Pale, J. Sommer, Org. Lett. 2007, 9, 883;
124. A. C. Cunha, L. O. R. Pereira, R. O. P. de Souza, M. C. B. V. de Souza, V. F. Ferreira, Nucleosides Nucleotides Nucleic Acids 2001, 20, 1555;
125. B. H. M. Kuijpers, S. Groothuys, A. R. Keereweer, P. J. L. M. Quaedflieg, R. H. Blaauw, F. L. van Delft, F. P. J. T. Rutjes, Org. Lett. 2004, 6, 3123;
126. J. L. M. Abboud, C. Foces-Foces, R. Notario, R. E. Trifonov, A. P. Volovodenko, V. A. Ostrovskii, I. Alkorta, J. Elguero, Eur. J. Org. Chem. 2001, 3013;
127. M. S. Raghavendra, Y. Lam, Tetrahedron Lett. 2004, 45, 6129;
128. P. Norris, D. Horton, B. R. Levine, Heterocycles 1996, 43, 2643.
129. F. Hammerschmidt, J.-P. Polsterer, E. Zbiral, Synthesis 1995, 415.