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2013 , Vol. 33 >Issue 08: 1769 - 1773

DOI: https://doi.org/10.6023/cjoc201301066

研究论文

多聚赖氨酸的合成及其微结构对pH的响应

  • 吴生蓉 ,
  • 耿欣 ,
  • 陈才 ,
  • 蔡亦康 ,
  • 韩国志
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  • 南京工业大学理学院 南京 210009

收稿日期: 2013-01-25

  修回日期: 2013-03-15

  网络出版日期: 2013-04-09

基金资助

中国博士后基金(No. 20100481084)资助项目.

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Synthesis of Poly-L-lysine and Its Structural Response to Environmental pH

  • Wu Shengrong ,
  • Geng Xin ,
  • Chen Cai ,
  • Cai Yikang ,
  • Han Guozhi
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  • College of Science, Nanjing University of Technology, Nanjing 210009

Received date: 2013-01-25

  Revised date: 2013-03-15

  Online published: 2013-04-09

Supported by

Project supported by the Postdoctoral Foundation of China (No. 20100481084).

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摘要

以L-赖氨酸为起始原料, 通过4步反应合成了多聚赖氨酸(Polylysine, PLL), 采用红外、核磁对其结构进行了表征, 并对关键合成环节进行了优化. 在此基础上, 通过扫描电镜和圆二色光谱研究了多聚赖氨酸分子在不同pH条件下的聚集行为, 并对机制进行了阐述. 研究结果表明, 多聚赖氨酸结构对环境酸碱度有不同的响应, 不同的pH条件下会导致不同的分子组装和形貌, 在酸性条件下PLL呈现一种特定的线圈形态; 碱性条件下呈现有序的松针状.

关键词： 多聚赖氨酸; Nε-苄氧羰基-L-赖氨酸-N-羧酸酐(NCA); 合成; pH; 响应

本文引用格式

吴生蓉 , 耿欣 , 陈才 , 蔡亦康 , 韩国志 . 多聚赖氨酸的合成及其微结构对pH的响应[J]. 有机化学, 2013 , 33(08) : 1769 -1773 . DOI: 10.6023/cjoc201301066

Abstract

Using L-lysine as raw material, Polylysine (PLL) was synthesized through four steps. The structures of intermediums and the final product were confirmed by IR and 1H NMR. Furthermore, some key synthetic steps were optimized in the process. On the basis, response ability to environmental pH of PLL structures was investigated by SEM and circular dichroism spectra. Experimental results indicated that polypeptide structure of PLL has good response ability to pH of environment. Under different pH conditions, distinct morphology was formed. Under acidic conditions, PLL presented a specific coil conformation, whereas orderly pine needle was observed under alkaline conditions.

Key words： polylysine; N-carboxy-(Nε-benzyloxycarbonyl)-L-lysine anhydride (NCA); synthesis; pH; response

参考文献

[1] Kito, Y.; Hiramot, S.; Murao, M.; Horio, Y.; Miyazaki, T.; Kodama, T.; Hakabou, Y. J. Nutr. 2003, 133(6), 1887.
[2] Quirk, R. A.; Chan, W. C.; Davies, M. C.; Tendler, S. J. B.; Shakesheff, K. M. M. Materials 2001, 22(8), 865.
[3] Vande Vondele, S.; Vörös, J.; Hubbell, J. A. Biotechnol. Bioeng. 2003, 82(7), 784.
[4] Hiraki, J. Fine Chem. 2000, 29(6), 18.
[5] Guo, Y.; Xia, F.; Xu, L.; Li, J.; Yang, W.-S.; Jiang, L. Langmuir 2010, 26(2), 1024.
[6] Wang, Y.; Chang, Y. C. Macromolecules 2003, 36, 6511.
[7] Isidro-Llobet, A.; Alvarez, M.; Albericio, F. Chem. Rev. 2009, 109, 2455.
[8] Kuwata, S.; Watanabe, H. Bull. Chem. Soc. Jpn. 1965, 38, 676.
[9] Isidro-Llobet, A.; Alvarez, M.; Albericio, F. Chem. Rev. 2009, 109, 2455.
[10] Bycroft,B.W.; Chan, W. C.; Chhabra, S. R.; Hothi, B.; Evans, D.; White, J. P. D. J. Chem. Soc., Chem. Commun. 1993, (9), 778.
[11] Huang, W.-D.; Chen, C.-Q. Polypeptide Synthesis, Science Press, Beijing, 1985, p. 59 (in Chinese).
(黄惟德, 陈常庆, 多肽合成, 科学出版社, 北京, 1985, p. 59.)
[12] Zhang, L.-Z.; You, G.; An, L.; Xue, Y.-S.; Mou, J.; Liu, M.; Liu, Y. Chin. J. Org. Chem. 2011, 31, 1475 (in Chinese).
(张玲, 郑友广, 安琳, 薛运生, 牟杰, 刘玲, 刘毅, 有机化学, 2011, 31, 1475.)
[13] Wendelmoed, N. E.; Wolthuis, D.; Water, L.; Wetering, P.; Mies Steenbergen, J.; Bosch, J.; Kettenes V.; Schuyl, W. J.; Hennink, W. E. Macromol. Chem. Phys. 1997, 198, 3893.
[14] Hatano, M.; Yoneyama, M. J. Am. Chem. Soc. 1970, 3, 1392.
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