摘要
目的:设计、合成并表征6个壳聚糖衍生物N-棕榈酰基-N′-氨基酰基壳聚糖。方法:分别选取甘氨酸、苯丙氨酸和脯氨酸为亲水链,棕榈酸为疏水链接枝到相对分子质量为70 kD和29 kD的壳聚糖上以形成两亲性壳聚糖衍生物N-棕榈酰基-N′-氨基酰基壳聚糖,采用IR,1H NMR和13C NMR对其结构进行表征。结果和结论:合成了6个壳聚糖衍生物,分别为:N-棕榈酰基-N′-甘氨酰基壳聚糖(70kCS-Gly-Pal,29kCS-Gly-Pal)、N-棕榈酰基-N′-苯丙氨酰基壳聚糖(70kCS-Phe-Pal,29kCS-Phe-Pal)和N-棕榈酰基-N′-脯氨酰基壳聚糖(70kCS-Pro-Pal,29kCS-Pro-Pal)。棕榈酰基(Pal)、甘氨酰基(Gly)、苯丙氨酰基(Phe)和脯氨酰基(Pro)的取代度通过1H NMR计算得出。其中N-棕榈酰基-N′-甘氨酰基壳聚糖(70kCS-Gly-Pal,29kCS-Gly-Pal)具有良好的水溶性。
Aim： To design, synthesize and characterize six N-palmityl-N′-aminoacyl chitosan derivatives potentially used as drug carriers. Methods： Firstly, glycine, L-phenylalanine and L-proline were chosen as the hydrophilic groups to graft chitosan. Palmitic acid as the hydrophobic group reacted with the modified chitosan. N-palm- ityl-N′-aminoacyl chitosan derivatives were obtained and confirmed with IR, ^1H NMR and ^13C NMR. Results and Conclusion： Six chitosan derivatives were synthesized in all, N-palmityl-N′-glycyl chitosan（70kCS-Gly-Pal, 29kCS-Gly-Pal）, N-palmityl-N′-phenylalanyl chitosan （70kCS-Phe-Pal, 29kCS-Phe-Pal）, N-palmityl-N′-prolyl chitosan （ 70kCS-Pro-Pal, 29kCS-Pro-Pal）. Among them, N-palmityl-N′-glycyl chitosan （ 70kCS-Gly-Pal, 29kCS- Gly-Pal） had good water-solubility. Besides that, the degrees of substitution of palmityl（Pal）, glycyl（Gly）, phenylalanyl（Phe） and prolyl（Pro） were calculated by ^1H NMR, and aqueous soluble chitosan derivatives may be used as drug carriers.
出处
《中国药科大学学报》
CAS
CSCD
北大核心
2009年第1期21-25,共5页
Journal of China Pharmaceutical University
基金
教育部科学技术研究重点资助项目(No.107062)
教育部新世纪人才支持计划资助项目(NCET-06-0499)~~
关键词
壳聚糖
两亲性
氨基酸
棕榈酸
合成
表征
chitosan
amphiphilicity
amino acid
palmitic acid
synthesis
characterization
