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

Research output: Contribution to journalArticle

37 Citations (Scopus)

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
StatePublished - 1977
Externally publishedYes

Fingerprint

Arginine Vasopressin
Cysteine
Resins
Chromatography
Byproducts
Amino Acids
Peptides
Monitoring
Liquids
benzhydrylamine
picric acid

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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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.",
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AU - Agosta, William C.

AU - Cowburn, David

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