The synthesis and some pharmacological properties of tocinoic acid and deaminotocinoic acid

Victor J Hruby, Clark W. Smith, David K. Linn, Martha F. Ferger, Vincent Du Vigneaud

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Tocinoic acid, the 20-membered cyclic disulfide ring of cysteinyltyrosylisoleucylglutaminylasparaginylcysteine, which possesses the tocin ring of oxytocin, was synthesized by the stepwise p-nitrophenyl ester method. All protecting groups of the protected intermediate Z-Cys(Bzl)-Tyr-Ile-Gln-Asn-Cys(Bzl)-ONB were removed on addition of this peptide to Na in NH3. The reduced peptide was converted to purified tocinoic acid by oxidation, followed by partition chromatography and gel filtration. Deaminotocinoic acid was synthesized by similar methods. No C-terminal carboxamide derivatives could be detected. Tocinoic acid possessed 0.2-0.3 unit/mg of oxytocic activity and no detectable avian vasodepressor activity, while deaminotocinoic acid had 3.7 ± 0.3 units/mg of oxytocic activity and no detectable avian vasodepressor activity. Deaminotocinoic acid possessed a slight inhibitory effect on the avian vasodepressor activity of synthetic oxytocin.

Original languageEnglish (US)
Pages (from-to)5478-5480
Number of pages3
JournalJournal of the American Chemical Society
Volume94
Issue number15
StatePublished - 1972

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Oxytocics
Pharmacology
Oxytocin
Acids
Peptides
Chromatography
Disulfides
Gel Chromatography
Esters
Gels
Derivatives
Oxidation
tocinoic acid

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

The synthesis and some pharmacological properties of tocinoic acid and deaminotocinoic acid. / Hruby, Victor J; Smith, Clark W.; Linn, David K.; Ferger, Martha F.; Du Vigneaud, Vincent.

In: Journal of the American Chemical Society, Vol. 94, No. 15, 1972, p. 5478-5480.

Research output: Contribution to journalArticle

Hruby, VJ, Smith, CW, Linn, DK, Ferger, MF & Du Vigneaud, V 1972, 'The synthesis and some pharmacological properties of tocinoic acid and deaminotocinoic acid', Journal of the American Chemical Society, vol. 94, no. 15, pp. 5478-5480.
Hruby, Victor J ; Smith, Clark W. ; Linn, David K. ; Ferger, Martha F. ; Du Vigneaud, Vincent. / The synthesis and some pharmacological properties of tocinoic acid and deaminotocinoic acid. In: Journal of the American Chemical Society. 1972 ; Vol. 94, No. 15. pp. 5478-5480.
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