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International Journal of Polymer Science
Volume 2011, Article ID 381076, 7 pages
http://dx.doi.org/10.1155/2011/381076
Research Article

Fast and Convenient Synthesis of Amine-Terminated Polylactide as a Macroinitiator for -Benzyloxycarbonyl-L-Lysine-N-Carboxyanhydrides

Key Laboratory for Ultrafine Materials of Ministry of Education, School of Materials Science and Engineering, East China University of Science and Technology, Shanghai 200237, China

Received 26 May 2011; Accepted 29 June 2011

Academic Editor: Shanfeng Wang

Copyright © 2011 Mingjie Ju et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. T. Ouchi, T. Uchida, H. Arimura, and Y. Ohya, “Synthesis of poly(L-lactide) end-capped with lactose residue,” Biomacromolecules, vol. 4, no. 3, pp. 477–480, 2003. View at Publisher · View at Google Scholar · View at Scopus
  2. F.-Z. Lu, X.-Y. Xiong, Z.-C. Li, F.-S. Du, B.-Y. Zhang, and F.-M. Li, “A convenient method for the synthesis of amine-terminated poly(ethylene oxide) and poly(ε-caprolactone),” Bioconjugate Chemistry, vol. 13, no. 5, pp. 1159–1162, 2002. View at Publisher · View at Google Scholar · View at Scopus
  3. P.-R. Ashton, S.-E. Boyd, C.-L. Brown et al., “Synthesis of glycodendrimers by modification of poly(propylene imine) dendrimers,” Chemistry, vol. 3, no. 6, pp. 974–984, 1997. View at Google Scholar · View at Scopus
  4. P. Degee, P. Dubois, R. Jerome, and P. Teyssie, “Macromolecular engineering of polylactones and polylactides. 9. Synthesis, characterization, and application of ω-primary amine poly (ε-caprolactone),” Macromolecules, vol. 25, no. 17, pp. 4242–4248, 1992. View at Google Scholar
  5. M. Gotsche, H. Keul, and H. Höcke, “Amino-termined poly (L-lactide)s as initiators for the polymerization of N-carboxyanhydrides: synthesis of poly(L-lactide)-block-poly(α-amino acid)s,” Macromolecular Chemistry and Physics, vol. 196, no. 12, pp. 3891–3903, 1995. View at Google Scholar
  6. S. Caillol, S. Lecommandoux, A.-F. Mingotaud et al., “Synthesis and self-assembly properties of peptide-polylactide block copolymers,” Macromolecules, vol. 36, no. 4, pp. 1118–1124, 2003. View at Publisher · View at Google Scholar · View at Scopus
  7. N. Kang and J.-C. Leroux, “Triblock and star-block copolymers of N-(2-hydroxypropyl)methacrylamide or N-vinyl-2-pyrrolidone and d,l-lactide: synthesis and self-assembling properties in water,” Polymer, vol. 45, no. 26, pp. 8967–8980, 2004. View at Publisher · View at Google Scholar · View at Scopus
  8. Y. F. Fan, G. Chen, J. Tanaka, and T. Tateishi, “L-Phe end-capped poly(L-lactide) as macroinitiator for the synthesis of poly(L-lactide)-b-poly(L-lysine) block copolymer,” Biomacromolecules, vol. 6, no. 6, pp. 3051–3056, 2005. View at Publisher · View at Google Scholar · View at Scopus
  9. M.-L Yuan and X.-M Deng, “Synthesis and characterization of poly(ethylene glycol)-block-poly(amino acid) copolymer,” European Polymer Journal, vol. 37, no. 9, pp. 1907–1912, 2001. View at Publisher · View at Google Scholar · View at Scopus
  10. Z.-G Yang, J. Yuan, and S.-Y Cheng, “Self-assembling of biocompatible BAB amphiphilic triblock copolymers PLL(Z)-PEG-PLL(Z) in aqueous medium,” European Polymer Journal, vol. 41, no. 2, pp. 267–274, 2005. View at Publisher · View at Google Scholar · View at Scopus
  11. H.-Y. Tian, C. Deng, H. Lin et al., “Biodegradable cationic PEG-PEI-PBLG hyperbranched block copolymer: synthesis and micelle characterization,” Biomaterials, vol. 26, no. 20, pp. 4209–4217, 2005. View at Publisher · View at Google Scholar · View at Scopus
  12. C. Deng, H. Tian, P. Zhang, J. Sun, X.-S. Chen, and X.-B. Jing, “Synthesis and characterization of RGD peptide grafted poly(ethylene glycol)-b-poly(L-lactide)-b-poly(L-glutamic acid) triblock copolymer,” Biomacromolecules, vol. 7, no. 2, pp. 590–596, 2006. View at Publisher · View at Google Scholar · View at Scopus
  13. C. Deng, X. Chen, H. Yu, J. Sun, T. Lu, and X. Jing, “A biodegradable triblock copolymer poly(ethylene glycol)-b-poly(l-lactide)-b-poly(l-lysine): synthesis, self-assembly, and RGD peptide modification,” Polymer, vol. 48, no. 1, pp. 139–149, 2007. View at Publisher · View at Google Scholar · View at Scopus
  14. J. Rao, Z. Luo, Z. Ge, H. Liu, and S. Liu, “‘Schizophrenic’ micellization associated with coil-to-helix transitions based on polypeptide hybrid double hydrophilic rod-coil diblock copolymer,” Biomacromolecules, vol. 8, no. 12, pp. 3871–3878, 2007. View at Publisher · View at Google Scholar · View at Scopus
  15. D.-K. Gilding and A. M. Reed, “Biodegradable polymers for use in surgery-poly(ethylene oxide) poly(ethylene terephthalate) (PEO/PET) copolymers: 1,” Polymer, vol. 20, no. 12, pp. 1454–1458, 1979. View at Google Scholar · View at Scopus
  16. D.-W. Grijpma, G.-J. Zondervan, and A.-J. Pennings, “High molecular weight copolymers of L-lactide and ε-caprolactone as biodegradable elastomeric implant materials,” Polymer Bulletin, vol. 25, no. 3, pp. 327–333, 1991. View at Publisher · View at Google Scholar · View at Scopus
  17. H.-R. Kricheldorf and J. Meier-Haack, “Polylactones, 22 ABA triblock copolymers of L-lactide and poly (ethylene glycol),” Macromolecular Chemistry and Physics, vol. 194, no. 2, pp. 715–725, 1993. View at Google Scholar
  18. A.-C. Albertsson and M. Gruvegård, “Degradable high-molecular-weight random copolymers, based on ε-caprolactone and 1,5-dioxepan-2-one, with non-crystallizable units inserted in the crystalline structure,” Polymer, vol. 36, no. 5, pp. 1009–1016, 1995. View at Google Scholar · View at Scopus
  19. Y.-J. Du, P.-J. Lemstra, A.-J. Nijenhuis, A.-M. Van Aert, and C. Bastiaansen, “ABA type copolymers of lactide with poly(ethylene glycol). Kinetic, mechanistic, and model studies,” Macromolecules, vol. 28, no. 7, pp. 2124–2132, 1995. View at Google Scholar · View at Scopus
  20. A. Schindler, Y.-M. Hibionada, and C.-G. Pitt, “Aliphatic polyesters. III. Molecular weight and molecular weight distribution in alcohol-initiated polymerizations of ε-caprolactone,” Journal of polymer science: Part A, vol. 20, no. 2, pp. 319–326, 1982. View at Google Scholar · View at Scopus
  21. X.-C. Zhang, D.-A. Macdonald, M.-F.-A. Goosen, and K.-B. Mcauley, “Mechanism of lactide polymerization in the presence of stannous octoate: the effect of hydroxy and carboxylic acid substances,” Journal of Polymer Science: Part A, vol. 32, no. 15, pp. 2965–2970, 1994. View at Google Scholar · View at Scopus
  22. A.-J. Nijenhuis, D.-W. Grijpma, and A.-J. Pennings, “Lewis acid catalyzed polymerization of L-lactide. Kinetics and mechanism of the bulk polymerization,” Macromolecules, vol. 25, no. 24, pp. 6419–6424, 1992. View at Google Scholar · View at Scopus
  23. M. Ryner, K. Stridsberg, A.-C. Albertsson, H. Von Schenck, and M. Svensson, “Mechanism of ring-opening polymerization of 1,5-dioxepan-2-one and L-lactide with stannous 2-ethylhexanoate. A theoretical study,” Macromolecules, vol. 34, no. 12, pp. 3877–3881, 2001. View at Publisher · View at Google Scholar · View at Scopus
  24. A. Kowalski, A. Duda, and S. Penczek, “Mechanism of cyclic ester polymerization initiated with tin(II) octoate. 2. 1 macromolecules fitted with tin(II) alkoxide species observed directly in MALDI-TOF spectra,” Macromolecules, vol. 33, no. 3, pp. 689–695, 2000. View at Google Scholar · View at Scopus
  25. D. S. Porche, M. Moore, and J. L. Bowles, “An unconventional method for the prepration of NCAs,” Synthetic Communications, vol. 29, pp. 843–852, 1999. View at Google Scholar
  26. Y. Kakizawa, A. Harada, and K. Kataoka, “Glutathione-sensitive stabilization of block copolymer micelles composed of antisense DNA and thiolated poly(ethylene glycol)-block-poly(L-lysine): a potential carrier for systemic delivery of antisense DNA,” Biomacromolecules, vol. 2, no. 2, pp. 491–497, 2001. View at Publisher · View at Google Scholar · View at Scopus
  27. S. Park and K. E. Healy, “Nanoparticulate DNA packaging using terpolymers of poly (lysine-g-(lactide-b-ethylene glycol)),” Bioconjugate Chemistry, vol. 14, no. 2, pp. 311–319, 2003. View at Publisher · View at Google Scholar · View at Scopus