An efficient acetylation of dextran using in situ activated acetic anhydride with iodine

被引:20
作者
Hussain, Muhammad A. [1 ]
Shahwar, Dure [1 ]
Tahir, Muhammad N. [2 ]
Sher, Muhammad [1 ]
Hassan, Muhammad N. [1 ]
Afzal, Zakia [1 ]
机构
[1] Univ Sargodha, Dept Chem, Sargodha 40100, Pakistan
[2] Johannes Gutenberg Univ Mainz, Inst Inorgan & Analyt Chem, D-55099 Mainz, Germany
关键词
acetic anhydride; acetylation; dextran; iodine; polysaccharide; UNCONVENTIONAL SYNTHESIS; CELLULOSE ESTERS; DERIVATIVES; MICROSPHERES; ADSORPTION; ACETATE;
D O I
10.2298/JSC1002165H
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A facile, efficient, cost-effective and solvent-free acetylation method has been developed for the acetylation of dextran. Dextran acetates were successfully synthesized using different molar ratios of acetic anhydride in the presence of iodine as a catalyst Without the use of any solvent. The reactions were realized at 50 degrees C for 3 h under stirring and nitrogen. This efficient method yielded highly pure and organosoluble dextran esters. The reaction appears highly effective for obtaining higher degrees of substitution (DS) with great efficiency. Under solvent-free conditions, dextran triacetates were efficiently synthesized. It was also observed that the molar ratio can easily control the DS of pendant groups onto the polymer backbone. Hence, a range of products With varying DS were Successfully designed, purified and characterized. Covalent attachment of the pendant groups onto the polymer backbone was verified by spectroscopic techniques. Thermogravimetric analysis indicated that the obtained dextran esters were thermally its stable as dextran. The DS of the pendant groups onto the polymer backbone was calculated using standard acid base titration after saponification. Furthermore, all products were thoroughly characterized by thermal analysis (TG and DTG), and FT-IR and H-1-NMR spectroscopic analysis.
引用
收藏
页码:165 / 173
页数:9
相关论文
共 25 条
[1]   An easy approach for the acetylation of saccharidic alcohols. Applicability for regioselective protections [J].
Adinolfi, M ;
Barone, G ;
Iadonisi, A ;
Schiattarella, M .
TETRAHEDRON LETTERS, 2003, 44 (25) :4661-4663
[2]  
AVRAMOGLOU DL, 2002, BIOCHEM PHARMACOL, V63, P129
[3]   Low-molecular-weight dextran derivatives (f-CMDB) enter the nucleus and are better cell-growth inhibitors compared with parent CMDB polymers [J].
Bittoun, P ;
Avramoglou, T ;
Vassy, J ;
Crépin, M ;
Chaubet, F ;
Fermandjian, S .
CARBOHYDRATE RESEARCH, 1999, 322 (3-4) :247-255
[4]  
CARVALHO D, 2001, SHOCK, V15, P157
[5]   Biodegradable dextran-based microspheres for delivery of anticancer drug mitomycin C [J].
Cheung, RY ;
Ying, YM ;
Rauth, AM ;
Marcon, N ;
Wu, XY .
BIOMATERIALS, 2005, 26 (26) :5375-5385
[6]  
Dhaneshwar Suneela S., 2006, Indian Journal of Pharmaceutical Sciences, V68, P705
[7]   Unconventional cellulose esters: synthesis, characterization and structure - property relations [J].
Heinze, T ;
Liebert, TF ;
Pfeiffer, KS ;
Hussain, MA .
CELLULOSE, 2003, 10 (03) :283-296
[8]   RETRACTED: Tumor targeting of gene expression through metal-coordinated conjugation with dextran (Retracted article. See vol. 232, pg. 266, 2016) [J].
Hosseinkhani, H ;
Aoyama, T ;
Ogawa, O ;
Tabata, Y .
JOURNAL OF CONTROLLED RELEASE, 2003, 88 (02) :297-312
[9]  
Hussain M. A., 2004, POLYM NEWS, V29, P14, DOI DOI 10.1080/00323910490980561
[10]   Acylation of cellulose with N,N′-carbonvldiimidazole-activated acids in the novel solvent dimethyl sulfoxide/tetrabutylammonium fluoride [J].
Hussain, MA ;
Liebert, T ;
Heinze, T .
MACROMOLECULAR RAPID COMMUNICATIONS, 2004, 25 (09) :916-920