Selective and full derivatization of amino group in chitosan with alkyl chloroformate of low stereo-hindrance

Zi-Wei Feng; Shao-Hua Huang; Wei Chen; Zheng-Wu Bai

Macromolecular Research, Vol.24, No.7, 650-653, July, 2016

DOI10.1007/s13233-016-4079-4 Export Citation

Selective and full derivatization of amino group in chitosan with alkyl chloroformate of low stereo-hindrance

Zi-Wei Feng, Shao-Hua Huang¹, Wei Chen, and Zheng-Wu Bai^†

School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan, 430073, P. R. China
¹Key Laboratory of Biobased Materials, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao, 266101, P. R. China

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Chitosan alkoxy formamide derivatives were prepared from chitosan of ultrahigh deacetylation degree via two-step reactions. It was found that amino groups in the chitosan were almost completely alkoxyformylated when low stereo-hindrance alkyl chloreformates were used as the modifying agents, while hydroxyls in chitosan were unreaaacted.

[References]

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[1] Krishna A, Sailaja, Amareshwar P, Chakravarty P, J. Pharm. Chem. Biol. Sci., 1, 474 (2010)

[2] Hirano S, Yamamoto T, Hayashi M, Nishida T, Inui H, Agric. Biol. Chem., 54, 2719 (1990)

[3] Abdelaal MY, Sobahi TR, Al-Shareef HF, Int. J. Biol. Macromol., 55, 231 (2013)

[4] Suyanto, Koesoemo HD, Ruriyanti R, Anggara LS, J. Chem. Pharm. Res., 7, 260 (2015)

[5] Aiba S, Makromol. Chem., 194, 65 (1993)

[6] Cardenas G, Paredes JC, Cabrera G, Casals P, J. Appl. Polym. Sci., 86(11), 2742 (2002)

[7] Yamamoto C, Hayashi T, Okamoto Y, J. Chromatogr. A, 1021, 83 (2003)

[8] Yamamoto C, Okamoto Y, Bull. Chem. Soc. Jpn., 77, 227 (2004)

[9] Yamamoto C, Yashima E, Okamoto Y, Bull. Chem. Soc. Jpn., 72, 1815 (1999)

[10] Yamamoto C, Yashima E, Okamoto Y, J. Am. Chem. Soc., 124(42), 12583 (2002)

[11] Shen J, Ikai T, Okamoto Y, J. Chromatogr. A, 1217, 1041 (2010)

[12] Kasat RB, Wang NHL, Franses EI, Biomacromolecules, 8(5), 1676 (2007)

[13] Zhang L, Shen J, Zuo W, Okamoto Y, J. Chromatogr. A, 1365, 86 (2014)

[14] Chen W, Bin Q, Bai Z, Zhou X, Xie X, Chin. J. Polym. Sci., 31, 1725 (2013)

[15] Chen W, Duan R, Fan Q, Bai Z, Huang S, Chin. J. Polym. Sci., 32, 458 (2014)

[16] Chen W, Wang Z, Xie X, Zhou X, Bai ZW, Int. J. Polym. Sci., 2013, 1 (2013)

[17] Tang S, Bin Q, Wei W, Bai ZW, Huang SH, J. Chromatogr. A, 1440, 112 (2016)

[18] Tolaimate A, Desbrieres J, Rhazi M, Alagui A, Polymer, 44(26), 7939 (2003)

[19] Tahtat D, Uzun C, Mahlous M, Gueven O, Nucl. Instrum. Methods Phys. Res. Sect. B-Beam Interact. Mater. Atoms, 265, 425 (2007)

[20] Paulino AT, Simionato JI, Garcia JC, Nozaki J, Carbohydr. Polym., 64, 98 (2006)

[21] Muzzarelli RAA, Ilari P, Petrarulo M, Int. J. Biol. Macromol., 16, 177 (1994)

[22] Heux L, Brugnerotto J, Desbrieres J, Versali MF, Rinaudo M, Biomacromolecules, 1(4), 746 (2000)