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Synthesis and Some Biological Properties of 4-Valine-oxytocin and 1-Deamino-4-valine-oxytocin

Vincent du Vigneaud 1, George Flouret 1, and Roderich Walter 1

From the 1 From the Department of Biochemistry, Cornell University Medical College, New York, New York 10021

4-Valine-oxytocin and 1-deamino-4-valine-oxytocin, analogues of the posterior pituitary hormone containing a valine residue in place of the glutamine residue in position 4, have been synthesized by the p-nitrophenyl ester method of peptide synthesis and tested for pharmacological activity. The 4-valine-oxytocin possesses 140 units per mg of oxytocic activity and 240 units per mg of avian vasodepressor activity. The 1-deamino-4-valine-oxytocin, in which the free amino group on the half-cystine residue in position 1 of 4-valine-oxytocin is replaced by hydrogen, is a highly potent compound, possessing approximately 350 units of oxytocic activity and 800 units of avian vasodepressor activity per mg.

Submitted on December 6, 1965


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