Synthèse de la Lys⁸‐oxytocine (lysine‐vasotocine) et nouvelle synthèse de la lysine‐vasopressine

Abstract

Abstract N‐CBO‐ L ‐Glutaminyl‐ L ‐asparaginyl‐S‐benzyl‐ L ‐cysteinyl‐azide has been condensed with L‐prolyl‐ϵ‐N‐tosyl‐ L ‐lysyl‐glycinamide, giving N‐CBO‐ L ‐glutaminyl L‐asparaginyl‐S‐benzyl‐ L ‐cysteinyl‐ L ‐prolylϵ‐N‐tosyl‐ L ‐lysyl‐glycinamide, which after spliting of the CBO‐protecting group has been condensed with N‐CBO‐S‐benzyl‐ L ‐cysteinyl‐ L ‐tyrosyl‐ L ‐isoleucyl‐azide. Cleavage of the protecting groups of the resulting nonapeptide with sodium in liquid ammonia, oxidation with air in dilute aqueous solution and purification by counter‐current distribution afforded Lys 8 ‐oxytocin, which represents a structural intermediate between oxytocin and lysine‐vasopressin and which exhibits the biological properties of both these natural hormones.