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

Abstract

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.

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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.

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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). https://doi.org/10.1007/BF00598080

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Keywords

  • Oxytocin
  • Hydrazide
  • DMFA
  • Protective Group
  • Trityl