Inactivation of lysine-vasopressin by acetone.

Abstract

During studies on the inactivation of oxytocin by acetone, a similar inactivation of lysine-vasopressin (Fig. 1) was also observed.1 In the reaction of oxytocin with acetone a new compound was formed which was isolated by partition chromatography on Sephadex G-25 and was referred to as "acetone-oxytocin." The studies indicated that lysine-vasopressin had formed a similar derivative with acetone. Further investigations on the "acetone-lysine-vasopressin," paralleling those carried out on "acetone-oxytocin," have been conducted and are presented in this communication.

Failure of Posterior Pituitary Hormone Samples of Low Metal Content To Produce Mitochondrial Swelling1

“…Material isolated from the main peak (R f 0.17, 65 mg from 101 mg of starting material) possessed a pressor activity of approximately 270 units/mg. This value compares favorably with that of the most potent samples of 8-lysine-vasopressin synthesized in this laboratory (8,9).…”

Neurophysin methylation in extracts of bovine posterior pituitary gland: Hormone binding ability

“…Coupling of vasopressin via the e-amino group of lysine to cyanogen bromide-activated Sepharose 4B (Pharmacia G.B. Ltd., UK) was achieved by reversibly protecting the o-amino group of the vasopressin [6] by formation of a vasopressin-acetone complex [7]. Protein binding at pH 5.8 to the agarose-coupled vasopressin was eluted with 50 mM formic acid.…”

Total synthesis of the diazaphenanthrene alkaloid perlolidine

“…After stirring for 15-30 min, the solution was poured into water and the pH adjusted to 5-6 with hydrochloric acid. A white solid precipitated, and this was recrystallized from ethanol to give an 85% yield of 2-aza-l-ketofluorenol with mp 250-251°; ir (KBr) 3260 (OH) and 1640 cm'1 (C=0); nmr (DMSO-ff6) 6.68 (d, 1, J = 7 Hz) and 7.60 (d, 1, / = 7 Hz) characteristic of the pyridone hydrogens, 7.50 (m, 4, aromatic hydrogens), and 5.45 (s, 1, HC-OH).…”

“…Since these transformations involve loss of the dimethoxyphenyl substituent,3,5 the structure of perlolidine (2) is defined.2 In the present paper we describe a total synthesis of this novel diazaphenanthrene alkaloid. 6 The pyridone 4 was an obvious intermediate for the synthesis of perlolidine. Once prepared, we planned to utilize the cyano group of 4 in the formation of the tricyclic diazaphenanthrene skeleton.…”

“…Journal of the American Chemical Society / 90:25 / December that condensation of ethyl cyanoacetate with the enamino ketone derived from benzoylacetone yielded 6-methyl-4-phenyl-2-pyridone, while the 2-pyridone possessing the reverse order of substituents was obtained upon reaction with malonamide. Thus the ethyl cyanoacetate reaction probably proceeded by way of 6 which subsequently cyclized to the desired pyridone 4. Hydrolysis and decarboxylation to 4-phenyl-2-pyridone confirmed the structure of the cyanopyridone 4.…”