NEW SYTHESIS OF VASOPRESSIN AND ITS DE-9-GLYCINE ANALOGS

Article abstract of DOI:10.1007/BF00598590

A unified scheme is proposed for the synthesis of <8-arginine>vasopressin (I), de-9-glycine<8-arginine>vasopressin (II), and de-9-glycinamide<8-arginine>vasopressin (III) which has been developed on the basis of the tetrapeptide Glm-Asn-Cys(Bzl)-Pro and other homologous fragments of neurohypophyseal hormones as common initial and intermediate compounds.The free dithiols obtained by the reduction of protected derivatives of (I)-(III) by sodium in liquid ammonia have been oxidized to the corresponding cyclic disulfides (I)-(III) with the aid of 1 M H2O2 at 0-5 deg C and pH (8.5.The vasopressor activities of (I)-(III) a re, respectively 470 +/- 20, 1.7, and 0.5 IU/mg (rat, in vivo).