Deuterated oxytocins: the synthesis and biological properties of a crystalline analog of deamino-oxytocin deuterated in the 5-asparagine position

Abstract

This paper describes the synthesis and biological activity of [5-L-asparagine-alpha,beta,beta-d(3)]-deamino-oxytocin. The model peptide S-benzyl-beta-mercaptopropionyl-L- asparaginyl-alpha,beta,beta-d(3)-glycinamide was also prepared to observe the effect of the conditions of peptide synthesis on the deuterium content. It was found that normal synthetic procedures could be used without a significant loss in the deuterium content.The [5-L-asparagine-alpha,beta,beta-d(3)]-deamino-oxytocin had, within experimental error, the same avian vasodepressor and oxytocic activities as deamino-oxytocin itself.