Synthesis of the N-terminal tripeptide sequence of oxytocin with various protective groups for the cysteine residue


The influence of the nature of the protective groups at the sulfur and nitrogen atoms in the cysteine molecule on the reactivity of this amino acid in the peptide condensation reaction has been investigated. The synthesis of the N-terminal tripeptide sequence of oxytocin was selected as a model reaction. For identifying the compounds synthesized and checking their purity, in addition to traditional physicochemical methods (TLC, melting points, angles of optical rotation), wide use has been made of the13C NMR method.

This is a preview of subscription content, access via your institution.

Literature cited

  1. 1.

    S. Ya. Miksta, An Investigation of New Methods of Protecting and Deblocking the Mercapto Group of Cysteine-Containing Peptides [in Russian], Dissertation for Candidate of Chemical Sciences, Riga (1987); Kh.-D. Yakubke and T. Kh. Eshkai, Amino Acids, Peptides, and Proteins [Russian translation], Mir, Moscow (1985), p. 100.

  2. 2.

    I. Photaki, J. Am. Chem. Soc.,88, No. 10, 2292 (1966).

    CAS  Article  Google Scholar 

  3. 3.

    E. Schroeder and K. Lübke, The Peptides, Academic Press, New York (1965) [Russian translation, Mir, Vol. 1 (1967), p. 9].

    Google Scholar 

  4. 4.

    O. W. Howarth and D. M. J. Lilley, Prog. NMR Spectrosc.,12, 1 (1978); V. I. Svergun, M. B. Smirnov, A. A. Antonov, E. P. Krysin, V. P. Panov, and T. Kh. Nikitina, Khim.-Farm. Zh., No. 5, 92 (1980); I. É. Zel'tser, S. P. Tikhomirova, E. P. Krysin, and M. B. Smirnov, Khim. Prir. Soedin., No. 3, 381 (1985).

    CAS  Article  Google Scholar 

  5. 5.

    A. K. Ivanov, V. N. Karel'skii, E. P. Krysin, E. É. Lavut, I. É. Zel'tser, and A. A. Antonov, Khim. Prir. Soedin., No. 1, 116 (1989).

  6. 6.

    G. C. Levy and G. L. Nelson, Carbon-13 Nuclear Magnetic Resonance for Chemists, Wiley, New York (1972) [Russian translation, Mir, Moscow (1975), p. 129].

    Google Scholar 

  7. 7.

    B. F. Pozdnev, Khim. Prir. Soedin., No. 6, 764 (1974).

  8. 8.

    L. Zervas and I. Photaki, J. Am. Chem. Soc.,84, 3887 (1962).

    CAS  Article  Google Scholar 

  9. 9.

    J. C. Sheehan, and D.-D. H. Yang, J. Am. Chem. Soc.,80, 1158 (1958).

    CAS  Article  Google Scholar 

Download references


Additional information

All-Union Scientific-Research Institute of the Technology of Blood Substitutes and Hormone Preparations, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 684–692, September–October, 1989.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Ivanov, A.K., Lavut, E.E., Antonov, A.A. et al. Synthesis of the N-terminal tripeptide sequence of oxytocin with various protective groups for the cysteine residue. Chem Nat Compd 25, 582–589 (1989).

Download citation


  • Oxytocin
  • Hydrazide
  • DMFA
  • Protective Group
  • Trityl