Synthesis of [1-(L-2-hydroxy-3-mercaptopropanoic acid)]oxytocin, a highly potent analogue of oxytocin

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Abstract
An analogue of oxytocin containing a hydroxy-group in place of the primary amino-group was synthesized by coupling p-nitrophenyl L-2-acetoxy-3-benzylthiopropanoyl-L-tyrosinate with a heptapeptide. [1-(L-2-Hydroxy-3-mercaptopropanoic acid)]oxytocin possessed three times the oxytocic activity of oxytocin on the isolated rat uterus. Neurophysin did not bind the new analogue.