A Rapid, Efficient Synthesis of Oxytocin and 8-Arginine-vasopressin. Comparison of Benzyl, p-Methoxybenzyl, and p-Methylbenzyl as Protecting Groups for Cysteine

David H. Live, William C. Agosta, David Cowburn

37 Scopus citations

Abstract

Oxytocin and 8-arginine-vasopressin have been synthesized in high yields in a short time using 1.5-fold molar excesses of protected amino acids by means of solid-phase synthesis on a benzhydrylamine resin. Coupling of each residue to the peptide resin was measured by automated picrate monitoring. High-pressure liquid partition chromatography was found to be extremely useful in characterizing products and by-products. Benzyl, p-methoxybenzyl, and p-methylbenzyl were compared as cysteine protecting groups in the syntheses, with the last two being preferred.

Original languageEnglish (US)
Pages (from-to)3556-3561
Number of pages6
JournalJournal of Organic Chemistry
Volume42
Issue number22
DOIs
Publication statusPublished - Oct 1 1977
Externally publishedYes

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ASJC Scopus subject areas

  • Organic Chemistry

Cite this

A Rapid, Efficient Synthesis of Oxytocin and 8-Arginine-vasopressin. Comparison of Benzyl, p-Methoxybenzyl, and p-Methylbenzyl as Protecting Groups for Cysteine. / Live, David H.; Agosta, William C.; Cowburn, David.

In: Journal of Organic Chemistry, Vol. 42, No. 22, 01.10.1977, p. 3556-3561.

Research output: Contribution to journalArticle