Scaled-up Synthesis and Characterization of Oxytocin Trisulfide

Robert P. Hammer, Melissa A. Butrie, Karen Davidson, Phillip T. Goldblatt, Alex M. Schrader, Joseph J. Dalluge, Allyn Becker, George Barany

Research output: Contribution to journalArticlepeer-review


The title peptide, oxytocin trisulfide (3), was required on a multi-100 mg scale, as part of an analytical method validation process for the clinically and commercially important product “Oxytocin Injection,” which is a sterile isotonic injectable formulation of oxytocin (2). We report here that previous chemistry from our academic laboratory can be successfully scaled up in the biotechnology sector to indeed provide pure 3 (overall yield 6–7%, > 95% purity). The scaled-up synthesis also gave rise, somewhat unexpectedly, to modest levels of oxytocin tetrasulfide (4), and even higher homologues. Protocols for synthesis, purification, and characterization [by HPLC, mass spectrometry and amino acid analysis] are described and discussed, along with possible mechanistic explanations for our findings.

Original languageEnglish (US)
Article number5
JournalInternational Journal of Peptide Research and Therapeutics
Issue number1
StatePublished - Jan 2024

Bibliographical note

Publisher Copyright:
© 2023, The Author(s), under exclusive licence to Springer Nature B.V.


  • Oxytocin (heterodectic intramolecular disulfide)
  • Oxytocin Tetrasulfide
  • Oxytocin Trisulfide
  • Scaled-up Peptide Synthesis


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