• 한국응용과학기술학회지
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• 제28권4호
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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.

• 환경위생공학
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• 제21권1호
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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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• 제56권4호
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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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• 제19권2호
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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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• 제9권1호
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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.

• 한국윤활학회:학술대회논문집
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• 한국윤활학회 2004년도 학술대회지
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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.

• 약학회지
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• 제42권6호
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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.

• 공업화학
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• 제7권1호
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• pp.118-128
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• 1996

양이온성 천연 고분자 전해질인 chitosan의 수용성 유도체를 제조하기 위해 chitosan에 먼저 Schiff's base를 형성시키고, 이를 다시 환원시키는 방법으로 chitosan에 N-methyl, N-butyl, N,N-dibutyl기를 각각 도입시킨 후, NMP중에서 methyl iodide를 이용하여 4차 ammonium 기가 도입된 chitosan 유도체를 합성하였다. 이 반응에서 선택적인 N-alkyl 유도체 뿐 아니라 O-alkyl 또한 진행됨을 확인하였다. 제조한 각 4 차 ammonium기가 도입된 chitosan 유도체의 응집성능을 검토하기 위해 제지공장 폐수를 대상으로 응집실험을 행한 결과, chitosan 에서와는 달리 거의 모든 pH 영역에서 일정하게 뛰어난 투과도와 COD 제거율을 보였으며, alkyl 기의 탄소수가 증가할수록 응집능은 증가되었고 그 중에서도 N-butyl dimethyl chitosan ammonium iodide가 가장 우수하였다. 그러나 N-dibutyl methyl chitosan ammonium iodide는 오히려 chitosan 자체보다 감소하는 경향을 나타내었다.

• KSTLE International Journal
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• 제5권2호
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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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• 제35권4호
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• pp.265-271
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• 1992

키틴과 키토산으로부터 carboxymethylchitin, acetylchitin, ethylchitosan, N-acetylchitosan 및 chitosansulfate를 합성하여 그 물리화학적 기능특성을 키틴 및 키토산과 비교 검토 하였다. Carboxymethylchitin은 물과 아세트산에 용해되었지만 ethylchitin은 아세트산에만 용해되었다. 보수력은 N-acetylchitosan이 1194%로 키틴에 비해 약 2배 정도 높았으며, 지방흡수력은 carboxymethylchitin이 1800%로 키틴 511%에 비해 월등히 높았다. Carboxymethylchitin의 유화성이 75.91%로 가장 높았으며 그 다음이 미세결정형 키틴으로 57.02%였으나 키틴 및 키토산은 유화성이 나타나지 않았다. 색소흡착능은 acetylchitin이 0.93 mg dye/g sample(Blue R-250), 0.96 mg dye/g sample(Red-2)로 키틴 및 키토산 보다 높았다. 따라서 carboxymethylchitin은 유화제로서, acetylchitosan은 색소흡착제로서 이용이 가능할 것으로 판단된다.