• Journal of the Korean Applied Science and Technology
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• v.28 no.4
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• pp.438-448
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• 2011

Chitosan is widely used in cosmetics and medical fields. Special emphasis has been put on the chemical modification of chitosan to explore its full potential. We have described the synthesis and biological activity of novel peptide amino acid derivatives. The polyamino acid derivatives were synthesized by introducing alkylamine functional group on chitosan at C-6. The poor aqueous solubility of chitosan derivatives hinder both pharmacological studies and pharmaceutical development. To make amino acid coupled chitosan derivatives with improved biological effect and solubility, some attempts have been taken to consist of amino peptide group like aspartic acid and phenylalanine-aspartic acid derivatives onto chitosan C-6. The resultingly substituted chitosan was characterized by solubility in various solvents. We measured chitosan derivatives with $^1H$-NMR and $^{13}C$-NMR. Also, We were investigated on the physical properties and biological activities of these products.

• Journal of environmental and Sanitary engineering
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• v.21 no.1 s.59
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• pp.21-34
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• 2006

To investigate anti-HIV-1 activity of water soluble chitosans, sulfated chitosan derivatives were prepared in mild condition. Various sulfated chitosan derivatives (N-3,6-O-S-chitosan, N-desulfated 3,6-O-S-chitosan, 3,6-O-S-chitin, and 3,6-O-sulfated-N-(o-carboxybenzoyl) chitosan) were synthesized with sulfurtrioxidepyridene complex in pyridine solvent. Characterization of the sulfated chitosan derivatives was carried out by $^{13}C$ NMR and IR spectroscopies. To observe ionic reaction properties, pKas of the sulfated chitosan derivatives and chitosan of low molecular weight were estimated by potentiometric titration. The sulfated chitosan derivatives had high water solubility, pKas (pKa : 7.7) of N-3,6-O-S-chitosan and N-desulfated 3,6-O-S-chitosan were increased than pKa of water insoluble chitosan (pKa : 6.2), These results suggest the participation of electrostatic interaction of amino and sulfate groups on the sulfated chitosans. Anti-HIV-1 drugs, such as AZT, ddC, and ddI for anti-HIV activity had higher selective index compared with SCB-chitosan but N-3,6-O-S-chitosan has shown higher selective index compared with ddC and ddI as HIV drugs.. These results suggest that sulfated chitosan derivatives were expected as an anti-HIV drug with differential driving force mechanism against some nucleoside analogs drug in the future.

• Elastomers and Composites
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• v.56 no.4
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• pp.254-263
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• 2021

In this study, chitosan obtained after varying extents of deacetylation (i.e., 10%, 30%, and 47%) was employed to introduce antibacterial properties to chitin. The deacetylation reaction completion, wherein the amino group content of chitin was reduced, was ascertained from the FT-IR and NMR analyses. The 47%-deacetylated chitosan exhibited superior antibacterial properties against Bacillus in a disk diffusion test. To further improve these properties, chitosan derivatives were grafted by acrylic acid and acrylamide. The varying concentrations of carboxyl groups, primary amines, and -CH₂-CH₂- with increasing acrylic acid and acrylamide contents were determined by FT-IR and NMR analyses. The enhanced antibacterial properties of the chitosan derivatives, owing to the increased acrylic acid and acrylamide contents, were revealed by the disk diffusion test. In particular, the derivatives with 1.3% acrylic acid and acrylamide showed the highest antibacterial activity, the bacterial reduction rate against Staphylococcus aureus and Escherichia coli being 99.9%, as observed through the ASTM E2149 standard test.

• Tribology and Lubricants
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• v.19 no.2
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• pp.72-77
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• 2003

Chitosan derivatives, Fluorinated chitosan, and N,N,N-Trimethyl chitosan iodide were synthesized as the disperse phases for the electrorheological fluid. The synthesis of these materials were confirmed by Fourier transform infrared spectroscopy (FT-lR). Chitosan derivative suspensions showed ER effect under the electric field. Especially, N,N,N-Trimethyl chitosan iodide suspension showed better electrorheological and electric properties than Fluorinated chitosan. It is due to difference in electron strength of polar groups composed derivatives. N,N,N-Trimethyl chitosan iodide suspension exhibited a linear dependence on an electric field power of 2.07.

• Journal of Life Science
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• v.9 no.1
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• pp.17-21
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• 1999

Chitosan derivitives, a sulfated N-acetylchitosan was synthesized, and artificial skin of sulfated N-acetylchitosan and N-carboxyl butyl chitosan were investigated. Sulfated derivatives of chitosan were analyzed by {TEX}${13}^C${/TEX}-NMR and the structure on N-acetyl chitosan 3,6-O-disulfate were confirmed. Rabbits underwent a midline laparotomy followed either by a bilateral peritoneal sidewall abraison(3.0×1.5cm). The injured surface was then covered with 0.2mm thick sulfated N-acetyl chitosan membrane. Sulfated N-acetyl chitosan membrane was found to reduce postsurgical bleeding after abraison of peritoneal surface treated with sulfated N-acetyl chitosan membrane. Sulfated N-acetyl chitosan implanted rabbit showed quick wound healing than N-carboxybutyl chitosan. With a sterilization procedure of chemical sterilization, sulfated N-acetyl chitosan seem to be better substitutes than N-carboxybutyl chitosan.

• Proceedings of the Korean Society of Tribologists and Lubrication Engineers Conference
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• 2004.11a
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• pp.323-329
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• 2004

The electrical and rheological properties pertaining to the electrorheological (ER) behavior of chitosan derivatives, chitosan, chitosan ammonium salt and chitosan phosphate suspensions in silicone oil were investigated. Chitosan derivative suspensions showed a typical ER response (Bingham flow behavior) upon application of an electric field. However, chitosan phosphate suspension exhibited an excellent shear yield stress compared with chitosan and chitosan ammonium salt suspensions. The difference in behavior results from the difference in the conductivity of the disperse phases due to the difference of their polarizability. The shear stress for the chitosan, chitosan ammonium salt and chitosan phosphate suspensions exhibited a linear dependence on the volume fraction of particles and 1.18 ,1.41 and 1.67 powers of the electric field. On the basis of the experimental results, the newly synthesized chitosan derivative suspensions found to be an ER fluid.

• YAKHAK HOEJI
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• v.42 no.6
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• pp.572-575
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• 1998

Chitosan has been known to have hypocholesterolemic and hypolipidemic effects in animal studies. Chitosan also absorbs bile acids in vitro and in vivo, which might result in the hypocholesterolemic action. Trialkyl chitosan derivatives were prepared and tested for bile acid absorption activity in vitro. The derivatives showed enhanced absorption capacities which were comparable to cholestyramine.

• Applied Chemistry for Engineering
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• v.7 no.1
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• pp.118-128
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• 1996

N-methyl, N-butyl and N,N-dibutyl chitosan derivatives were prepared by Schiff's base formation and hydrogenation in aqueous media. Furthermore quaternization of the chitosan derivatives was performed in N-methyl-2-pyrrolidone using methyl iodide to obtain water soluble cationic polyelectrolytes. It was confirmed that O-alkylation was occured as well as selective N-alkylation in these reactions. Chitosan and chitosan derivatives with quaternary ammonium iodide showed high flocculation power as the cationic flocculant. When tested on paper mill waste water, they showed high flocculation power, independing of pH range. The flocculation power was increased as the N-alkyl chain length was increased. Among them, N-butyl dimethyl chitosan ammonium iodide showed better flocculation power than chitosan. But, N,N-dibutyl-N-methyl chitosan ammonium iodide showed less flocculation powre than chitosan itself.

• KSTLE International Journal
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• v.5 no.2
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• pp.49-51
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• 2004

The electrical and rheological properties pertaining to the electrorheological (ER) behavior of chitosan derivatives, chitosan, chitosan ammonium salt and chitosan phosphated suspensions in silicone oil were investigated. Chitosan derivative suspensions showed a typical ER response (Bingham flow behavior) upon application of an electric field. However, chitosan phosphate suspension exhibited an excellent shear yield stress compared with chitosan and chitosan ammonium salt suspensions. The difference in behavior results from the difference in the conductivity of the disperse phases due to the difference of their polarizability. The shear stress for the chitosan, chitosan ammonium salt and chitosan phosphate suspensions exhibited a linear dependence on the volume fraction of particles and 1.18, 1.41 and 1.67 powers of the electric field. On athe basis of the experimental results, the newly synthesized chitosan dervative suspensions found to be an ER fluid.

• Applied Biological Chemistry
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• v.35 no.4
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• pp.265-271
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• 1992

Derivatives (microcrystalline chitin, carboxymethylchitin, acetylchitin, N-acetylchitosan, ethylchitosan and chitosansulfate) of chitin and chitosan were synthesized, and the physicochemical properties of the derivatives were compared with those of chitin and chitosan. Carboxymethylchitin was soluble in water or acetic acid, whereas chitosan and ethylchitosan were soluble in acetic acid alone. The water binding capacity of N-acetylchitosan was two fold higher than that of chitin. Lipid binding capacity of carboxymethylchitin was the highest, holding 1800%, and that of chitin was the lowest, holding 511% among the derivatives. Carboxymethylchitin among the derivatives showed the highest emulsifying capacity, however chitin and chitosan didn't produce emulsions. Dye binding capacity of acetylchitin was the highest, holding 0.93 mg dye/g sample (Blue R-250) and 0.96 mg dye/g sample (Red No. 2). It was concluded that carboxymethylchitin is a good emulsifier and N-acetylchitosan, chitosansulfate and chitosan are suitable for use as dye absorbents.