Oxytocin (OT) is a naturally-occurring human hormone and neurotransmitter that is involved in myriad physiological and psychological phenomenon. Produced in the hypothalamus, OT is a nonapeptide that possesses a single disulfide bond that is critical to both structure and function. In addition to administering OT to induce uterine contractions during childbirth, one common chemotherapeutic use of synthetic oxytocin is for the prevention of postpartum hemorrhage. For these healthcare applications, OT is stable at low temperature for prolonged supply chain storage. However, in areas without access to consistent refrigeration, use of OT is compromised, as disulfide-mediated decomposition occurs rapidly at ambient temperature. Highlighting the need for an improved thermostable OT derivative, carbetocin, which contains a disulfide to thioether substitution allows dramatically improved shelf life. Our research concerning photochemical construction of thioether linkages has facilitated improved synthetic access to carbetocin. Alongside structural characterization, functional analysis of our synthetic carbetocin was determined.<br/>

Synthesis of carbetocin using photochemical cyclization conditions

2019 Spring National Meeting

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