Letters in Peptide Science

, Volume 5, Issue 4, pp 259–262 | Cite as

Derivatives of aminoquinones with N-protected amino acids

  • Chrysostomos Pachatouridis
  • Elias A. Couladouros
  • Vassilios P. Papageorgiou
  • Maria Liakopoulou-Kyriakides


The synthesis of derivatives of aminoquinones with N-protected amino acids is reported here. 2-Amino-1,4-benzoquinone and 2-amino-1,4-naphthoquinone, prepared by the azide method in yields of 60 and 95% respectively, were coupled with N-Boc-protected amino acids including glycine, serine, proline and tyrosine, to give the correspondening derivatives.N, N′-Diisopropylcarbodiimide/1-hydroxybenzotriazole orN, N′-dicyclohexylcarbodiimide/HOBt used as coupling reagents provided the expected products in satisfactory yields and purities as supported by TLC, HPLC and spectral analysis.

Key words

aminoquinones N-Protected amino acids quinonyl-amino acids 


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  1. 1.
    Thomson, R.H., Naturally Occuning Quinones, 2nd ed., Academic press: New York, NY, 1971.Google Scholar
  2. 2.
    Janes, S.M., Mu, D., Wemmer, D., Smith, A. J., Kaur, S., Maltby, D., Burlingame and Kliman, J.P., Science, 248 (1990) 982.Google Scholar
  3. 3.
    Al-Massad, F.K., Kadir, F.H.A. and Moore, G.R., Biochem. J., 283 (1992) 177.PubMedGoogle Scholar
  4. 4.
    Blum, R.H. and Carter, S.K., Ann. Int. Med., 80 (1974) 249.PubMedGoogle Scholar
  5. 5.
    Nithianandam, V.S. and Erhan S., Polymer, 32 (1971) 1146.CrossRefGoogle Scholar
  6. 6.
    Kaleem, K., Chertok, F. and Erhan, S., Prog. Org. Coating, 15 (1987) 63.CrossRefGoogle Scholar
  7. 7.
    Couladouros, E.A., Plyta, Z.F. and Papageorgiou V.P., J. Org. Chem., 61 (1996) 3031.PubMedCrossRefGoogle Scholar
  8. 8.
    Lin, T.S., Xu, S. P., Zhu, L.Y., Cosby, L. and Sartorelli, A., J. Med. Chem., 32 (1989) 1467.PubMedCrossRefGoogle Scholar
  9. 9.
    Lin, T.S., Xu, S.P., Zhu, L.Y., Divo, A. and Sartorelli, A., J. Med. Chem., 34 (1991) 1634.PubMedCrossRefGoogle Scholar
  10. 10.
    Bade Shrestha-Dawadi, P., Bittner, S., Fridkin, M. and Rahimpour, S., Synthesis, 12 (1996) 1468.CrossRefGoogle Scholar
  11. 11.
    Rahimpour, S., Weiner, L., Fridkin, M., Bade Shrestha-Dawadi, P. and Bittner, S., Lett. Pept. Sci., 3 (1996) 263.CrossRefGoogle Scholar
  12. 12.
    Furusaki, A. and Watanabe, T., Chem Pharm. Bull., 21 (1973) 931 and references therein.PubMedGoogle Scholar
  13. 13.
    Lanz, T., Tropf, A., Marner, F.-J., Schroder, J. and Schroder, G., J. Biol. Chem., 266 (1991) 9971.PubMedGoogle Scholar
  14. 14.
    Parker, K. and Sworin, M., J. Org. Chem., 46 (1981) 3218.CrossRefGoogle Scholar
  15. 15.
    Aristoff, P. and Johnson, P., J. Org. Chem., 57 (1992) 6234.CrossRefGoogle Scholar

Copyright information

© Kluwer Academic Publishers 1998

Authors and Affiliations

  • Chrysostomos Pachatouridis
    • 1
  • Elias A. Couladouros
    • 2
  • Vassilios P. Papageorgiou
    • 1
  • Maria Liakopoulou-Kyriakides
    • 1
  1. 1.Department of Chemical EngineeringAristotle University of ThessalonikiThessalonikiGreece
  2. 2.Chemistry LaboratoriesAgricultural University of AthensAthensGreece

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