Macromolecular Research

The Polymer Society of Korea (한국고분자학회)
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The Solid-Phase Synthesis of Amino Acid-Derived Diacetylene Lipids

  • Kim Jong-Man (Department of Chemical Engineering, Hanyang University) ;
  • Park Bum Jun (Department of Chemical Engineering, Hanyang University) ;
  • Chang Eun-Ju (Department of Chemical Engineering, Hanyang University) ;
  • Yi Sung Chul (Department of Chemical Engineering, Hanyang University) ;
  • Suh Dong Hack (Department of Chemical Engineering, Hanyang University) ;
  • Ahn Dong June (Department of Chemical and Biological Engineering, Korea University)
  • Published : 2005.06.01
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Abstract

We prepared amino acid-derived diacetylene monomers using solid-phase organic synthesis. The solid-phase synthetic method allowed for the rapid and efficient preparation of functional diacetylenes. Amino acids having hydrophobic sidechains such as alanine, leucine, and phenylalanine, as well as hydrophilic sidechains such as aspartic acid and lysine, were successfully coupled to the diacetylene lipid. The diacetylene monomers prepared in this way were subjected to routine procedures for the generation of polydiacetylene vesicles. Depending on the nature of the side-chains, pink to blue colored polydiacetylenes were generated.

Keywords

References

  1. Chargy, J. O. Nagy, W. Spevak, and M. D. Bednarski, Science, 261, 585 (1993) https://doi.org/10.1126/science.8351525
  2. S. Okada, S. Peng, W. Spevak, and D. Charych, Ace. Chem. Res., 31, 229 (1998) https://doi.org/10.1021/ar970063v
  3. R. Jelinek, Drug. Develop. Res., 50, 497 (2000) https://doi.org/10.1002/1098-2299(200007/08)50:3/4<497::AID-DDR33>3.0.CO;2-U
  4. F. Reichel, A. M. Roelofsen, H. P. M. Geurts, S. J. van der Gaast, M. C. Feiters, and G.-J. Boons, J. Org. Chem., 65, 3357 (2000) https://doi.org/10.1021/jo991685s
  5. F. Z. Dorwald, Organic Synthesis on Solid Phase, Wiely-VCH, Weinheim, 2002
  6. D. J. Ahn, E.-H. Chae, K. S. Lee, H.-Y. Shim, T.-E. Chang, K.-D. Ahn, and J.-M. Kim, J. Am. Chem. Soc., 125, 8976 (2003) https://doi.org/10.1021/ja0299001
  7. J.-M. Kim, E.-K. Ji, S.-M. Woo, H. Lee, and D. J. Ahn, Adv. Mater., 15, 1118 (2003) https://doi.org/10.1002/adma.200304944
  8. J.-T. Cho, S.-M. Woo, D. J. Ahn, K.-D. Ahn, H. Lee, and J.-M. Kim, Chem. Lett., 32, 282 (2003) https://doi.org/10.1246/cl.2003.282
  9. E.-K. Ji, D. J. Ahn, and J.-M. Kim, Bull. Korean Chem. Soc., 24, 667 (2003) https://doi.org/10.5012/bkcs.2003.24.5.667
  10. R. E. Babine and S. L. Bender, Chem. Rev., 97, 1359 (1997) https://doi.org/10.1021/cr960370z
  11. D. Leung, G. Abbenante, and D. Fairlie, J. Med. Chem., 43, 305 (2000) https://doi.org/10.1021/jm990412m
  12. S. Liu and D. S. Edwards, Chem. Rev., 99, 2235 (1999) https://doi.org/10.1021/cr980436l