Four cyclic disulfide pentapeptides possessing the ring of vasopressin

Abstract

Pressinoic acid, the cyclic disulfide of cysteinyltyrosylphenylalanylglutaminylasparaginylcysteine which contains the pressin ring structure of the posterior pituitary hormones arginine-and lysine-vasopressin, has been synthesized by the stepwise p-nitrophenyl ester method. The closely related compounds deaminopressinoic acid, pressinamide, and deaminopressinamide have been synthesized by similar methods, and all have been tested for some of the biological activities shown by the parent hormones. None of the compounds showed any pressor or avian vasodepressor activities. All except pressinoic acid exhibited a slight degree of oxytocic activity, in the range of 0.05-0.5 unit/mg. No inhibitory properties were noted in the systems studied.

Nuclear Magnetic Resonance Studies of Lysine-Vasopressin: Structural Constraints

“…The LysVP (I) (2, 3), 1-deamino-4-decarboxamido-LysVP (II) (4), 4-decarboxamido-LysVP (III) (4), and 9-glycine methyl amide-LysVP (IV) (Glass, J., and V. du Vigneaud, manuscript in preparation) were purified preparations, each possessing its full pressor activity.t The following compounds were also used in this study: Z-Asn-Cys(Bzl)-Pro-Lys(Tos)-Gly-NH2 (V) (5), Z-Gln-OMe (VI) (6), Z-Gly-NH2 (VII) (7), Z-Sar-NH2 (VIII) (8), Z-Gln-Asn-Cys(Bzl)-OMe (IX) (9), pressinoic acid (H-Cys-Tyr-Phe-Gln-Asn-Cys-OH) (X) L____________ I (10), deaminopressinoic acid (XI) (10), and Z-Pro-Leu-Gly-NH2 (11).…”

[3H]9-desglycinamide,8-arginine vasopressin: metabolism and in-vivo fate

“…The final radiochemical purity of the tritiated peptide exceeded 95% and the specific activity was determined to be 9-0 Ci/mmol. Non-labelled DGAVP and its fragments AVP-( 1-7), AVP-0-6), [Cyt6]AVP-(2-8), [pGlu4,Cyt6]AVP-(4-8) and [Cyt6]AVP-(5-8) were synthesized and purified using described procedures (Ferger, Jones, Dyckes & du Vigneaud (1972) for the former three peptides and van Nispen, Hannink, Schoffelmeer et al (1984) for the latter three compounds). Their peptide contents varied from 71 to 89% and the purity of their main peptide components ranged between 92 and 98%.…”

A Semi-Automated <i>in vitro</i> Assay for CRF: Activities of Peptides Related to Oxytocin and Vasopressin

“…Arginine vasopressin, 4-threoninc-arginine vasopressin, deamino-4-thrconine-arginine vasopressin, 4-threonine-lysine vasopressin, and deamino-4-threonine-lysine vasopressin were used [Manning et at.. 1973a, b], as were pressinoic acid and its derivatives [Ferger et at., 1972] and locinoic acid and 4-serine-tocinoic acid derivatives [Hruby et at., 1972b). The peptides were received as crystalline solids, which were weighed out, dissolved in 0.1 n acetic acid to a concentration of 1 /<g//d, and stored in the refrigerator.…”