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Synthesis of the amide of the C-terminal tetrapeptide of the sequence of oxytocin

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The synthesis has been effected of the amide of the tetrapeptide forming the sequence 6–9 of oxytocin with the use of benzyl protection of the thiol function of cysteine by two main schemes 1+3 and 2+2. The advantageousness of performing the synthesis by the 2+2 scheme has been shown. The overall yield of tetrapeptide using the method of condensation with the formation of mixed anhydrides amounted to 51% by the scheme proposed.

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Literature cited

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    Zh. D. Bespalova et al., Khim. Prir. Soedin., 808 (1973); Zh. D. Bespalova et al., Zh. Obshch. Khim.,44, No. 1 (1973).

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    S. Ya. Miksta et al., Izv. Akad. Nauk, LatvSSR, Ser. Khim., No. 5, 618–621 (1975).

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Additional information

All-Union Scientific-Research Institute of the Technology of Blood Substitutes and Hormone Preparations, Moscow. Translated from Khimiya Prirodnykh Soedinenii, Nos. 3,4, pp. 393–400, May–August, 1992.

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Ivanov, A.K., Antonov, A.A. & Donetskii, I.A. Synthesis of the amide of the C-terminal tetrapeptide of the sequence of oxytocin. Chem Nat Compd 28, 344–349 (1992). https://doi.org/10.1007/BF00630256

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  • Organic Chemistry
  • Amide
  • Cysteine
  • Thiol
  • Anhydride