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Different approaches to synthesis of N-carboxyanhydrides of amides of trifunctional amino acids

  • Organic Synthesis and Industrial Organic Chemistry
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Abstract

Original method for synthesis of N-carboxyanhydrides of trifunctional α-amino acids containing substituents attached by amide bonds at the ω-functional group is suggested.

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References

  1. Zistler, A., Koch, S., and Schluter, A.D., J. Chem. Soc., Perkin Trans., 1999, vol. 1, pp. 501–508.

    Article  Google Scholar 

  2. Deng, H.-T., Xu, Z.-K., Wu, J., et al., J. Mol. Catal. B: Ensymatic, 2004, vol. 28, pp. 95–100.

    Article  CAS  Google Scholar 

  3. Cloninger, M.J., Current Opinion Chem. Biol., 2002, vol. 6, pp. 742–748.

    Article  CAS  Google Scholar 

  4. Girbasova, N.V., Migunova, I.I., Raspopova, I.R., and Bilibin, A.Yu., Vysokomol. Soedin., Ser. A, 2003, vol. 45, no. 4, pp. 550–561.

    CAS  Google Scholar 

  5. Sadler, K. and Tam, J.P., Rev. Mol. Biotechnol., 2002, vol. 90, pp. 195–229.

    Article  CAS  Google Scholar 

  6. Veprek, P. and Jezek, J., J. Peptide Sci., 1999, vol. 5, pp. 5–23.

    Article  CAS  Google Scholar 

  7. Sanda, F., Fujiyama, T., and Endo, T., J. Polym. Sci., Part A, 2001, vol. 39, pp. 732–741.

    Article  CAS  Google Scholar 

  8. Alyab’eva, V.P., Girbasova, N.V., and Bilibin, A.Yu., Vestn. SPb, Gos. Univ., 2006, Ser. 4, issue 3, pp. 95–105.

  9. Karnup, A.S., Uverskii, V.N., and Medvedkin, V.N., Bioorgan. Khim., 1996, vol. 22, no. 8, pp. 563–574.

    CAS  Google Scholar 

  10. Deming, T.J., Adv. Drug Delivery Rev., 2002, vol. 54, pp. 1145–1155.

    Article  CAS  Google Scholar 

  11. Aoi, K., Tsutsumiuchi, K., and Okada, M., Macromolecules, 1994, vol. 27, pp. 875–877.

    Article  CAS  Google Scholar 

  12. Obshchaya organicheskaya khimiya (General Organic Chemistry), vol. 3, Kochetkov, N.K., Ed., Moscow: Khimiya, 1982.

    Google Scholar 

  13. Yu, M., Novak, A.P., and Deming, T.J., J. Am. Chem. Soc., 1999, vol. 121, pp. 12210–12211.

    Article  CAS  Google Scholar 

  14. Fujita, Y., Koga, K., Kim, H.-K., et al., J. Polym. Sci., Part A, 2007, vol. 45. 5365–5369.

    Article  CAS  Google Scholar 

  15. Daly, W.H. and Poshй, D., Tetrahedron Lett., 1988, vol. 29, no. 46, pp. 5859–5842.

    Article  CAS  Google Scholar 

  16. Obshchaya organicheskaya khimiya (General Organic Chemistry), vol. 4, Kochetkov, N.K., Ed., Moscow: Khimiya, 1983.

    Google Scholar 

  17. Hirschmann, R., Schwam, H., Strachan, R.G., et al., J. Am. Chem. Soc., 1971, vol. 93, no. 10, pp. 2746–2754.

    Article  CAS  Google Scholar 

  18. Wilder, R. and Mobashery, Sh., J. Org. Chem., 1992, vol. 57, pp. 2755–2756.

    Article  CAS  Google Scholar 

  19. Carpino, L.A., Beyermann, M., Wenschuh, H., and Bienert, M., Acc. Chem. Res., 1996, vol. 29, pp. 268–274.

    Article  CAS  Google Scholar 

  20. Losse, G. and Wehrstedt, K.D., Z. Chem., 1981, vol. 121, p. 148.

    Google Scholar 

  21. Ueda, M., Washio, I., and Shibasaki, Y., Abstracts of Papers, 40th Int. Macromol. Symp., Paris, France, July. 2004.

  22. Weygand-Hilgetag Organisch-chemische Experimentierkunst, Hilgetag, G. and Martini, A., Eds., Leipzig: Johann Ambrosius Barth, 1964, 3rd ed.

    Google Scholar 

  23. Matsuda, F., Iton, Sh., Hatfori, N., et al., Tetrahedron, 1985, vol. 41, no. 18, pp. 3625–3631.

    Article  CAS  Google Scholar 

  24. Bilibin, A.Yu., Girbasova, N.V., Matsuk, A.V., et al., Vysokomol. Soedin., Ser. A, 2007, vol. 49, no. 4, pp. 581–592.

    CAS  Google Scholar 

  25. Goodman, M. and Peggion, E., Pure Appl. Chem., 1981, vol. 53, pp. 699–714.

    Article  CAS  Google Scholar 

  26. Gordon, A.J. and Ford, R.A., The Chemist’s Companion, New York: Wiley, 1972.

    Google Scholar 

  27. Ramalingam, K. and Woodard, R.W., J. Org. Chem., 1988, vol. 53, pp. 1900–1903.

    Article  CAS  Google Scholar 

  28. Gershkovich, A.A. and Kibirev, V.K., Sintez peptidov: Reagenty i metody (Synthesis of Peptides: Reagents and Methods), Kiev: Naukova dumka. 1987.

    Google Scholar 

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Authors and Affiliations

  1. St. Petersburg State University, St. Petersburg, Russia

    V. P. Alyab’eva, N. V. Girbasova & A. Yu. Bilibi

Authors
  1. V. P. Alyab’eva
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  2. N. V. Girbasova
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  3. A. Yu. Bilibi
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Additional information

Original Russian Text © V.P. Alyab’eva, N.V. Girbasova, A.Yu. Bilibi, 2009, published in Zhurnal Prikladnoi Khimii, 2009, Vol. 82, No. 4, pp. 612–618.

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Alyab’eva, V.P., Girbasova, N.V. & Bilibi, A.Y. Different approaches to synthesis of N-carboxyanhydrides of amides of trifunctional amino acids. Russ J Appl Chem 82, 605–612 (2009). https://doi.org/10.1134/S1070427209040144

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  • DOI: https://doi.org/10.1134/S1070427209040144

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