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

doi:10.1021/jo00442a025

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 journal › Article › peer-review

38 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 language	English (US)
Pages (from-to)	3556-3561
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	42
Issue number	22
DOIs	https://doi.org/10.1021/jo00442a025
State	Published - Oct 1 1977
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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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

PY - 1977/10/1

Y1 - 1977/10/1

N2 - 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.

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

Abstract

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