1-Mercaptoacetic Acid-4-β-alanine-oxytocin<sup>*</sup>

Jarvis, Derek; Manning, M.; Vigneaud, Vincent du

doi:10.1021/bi00857a001

Cited by 3 publications

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Impact of the Merrifield solid phase method on the design and synthesis of selective agonists and antagonists of oxytocin and vasopressin: A historical perspective

Manning

2008

Biopolymers

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This tribute to Bruce Merrifield traces the author's fortuitous path in 1964 from Vincent du Vigneaud's laboratory to the laboratory of D. W. Woolley to learn the solid phase method and then to his first faculty position in the Department of Biochemistry, McGill University, Montreal in 1965. It recalls the key roles played from early 1966 to July 1967 by Bruce Merrifield, John Stewart, Arnold Marglin, Herb Takashima, and Vincent du Vigneaud in providing key advice to the author's efforts to use the solid phase method to synthesize oxytocin; while simultaneously the du Vigneaud and Merrifield laboratories were collaborating on the solid phase synthesis of deamino‐oxytocin. Both syntheses were published in the same issue of the Journal of American Chemical Society in 1968. Also described is how this breakthrough impacted the author's scientific career: by leading to highly productive collaborative studies, initially with Wilbur H. Sawyer and subsequently with others, on the design and synthesis of selective agonists, antagonists, and radioiodinated ligands for oxytocin and vasopressin receptors. These syntheses were greatly facilitated by the contributions of highly talented graduate students, research technicians, and visiting peptide chemists from Hungary, England, Poland, Bulgaria, and China. Many of these peptides have become very valuable pharmacological tools in studies on the peripheral and central effects of oxytocin and vasopressin: further attesting to the profound impact of the solid phase method as the cornerstone for all the discoveries, which he and his collaborators and coworkers have made over the past 40 years. © 2007 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 90: 203–212, 2008.This article was originally published online as an accepted preprint. The “Published Online” date corresponds to the preprint version. You can request a copy of the preprint by emailing the Biopolymers editorial office at biopolymers@wiley.com

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Impact of the Merrifield solid phase method on the design and synthesis of selective agonists and antagonists of oxytocin and vasopressin: A historical perspective

Manning

2008

Biopolymers

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The Design of Peptide Hormone Analogs

Rudinger¹

1971

Drug Design

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STUDIES ON THE IMPORTANCE OF THE ASPARAGINE RESIDUE IN OXYTOCIN Synthesis and Some Pharmacological Properties of [1‐α‐Mercaptoacetic acid, 5‐isoasparagine] Oxytocin

Roy

Johnson

Dubin

et al. 1980

International Journal of Peptide and Protein Research

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1-a-Mercaptoacetic acid, 5-isoasparagine] oxytocin was synthesized to stud,v the effects of moving the side chain carboxamide group o f the amino acid residue in position 5 o f oxytocin from the /3 to the (Y position. The analog has an isoasparagine residue in position 5 and the 20-membered ring size of oxytocin is maintained by mbstituting cysteine in position 1 of oxytocin by amercaptoacetic ci~id. The analog was found to possess 0.098 2 0.002 U/mg of uterotonic activity but no milk-ejecting, antidiuretic or rat pressor activity could be detected. The substance did not inhibit the uterotonic or milk-ejectingactivity induced by oxytocir; nor the antidiuretic or rat pressor responses to the USP posterior pituitary standard. These results, together with the data available in the literature, indicate that an analog of oxytocin lacking the asparagine residue in position 5 is neither an agonist nor an antagonist. The observations may mean that the asparagine residue is critically important for the interaction of oxytocin with its receptor.

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1-Mercaptoacetic Acid-4-β-alanine-oxytocin^*

Cited by 3 publications

References 10 publications

Impact of the Merrifield solid phase method on the design and synthesis of selective agonists and antagonists of oxytocin and vasopressin: A historical perspective

Impact of the Merrifield solid phase method on the design and synthesis of selective agonists and antagonists of oxytocin and vasopressin: A historical perspective

The Design of Peptide Hormone Analogs

STUDIES ON THE IMPORTANCE OF THE ASPARAGINE RESIDUE IN OXYTOCIN Synthesis and Some Pharmacological Properties of [1‐α‐Mercaptoacetic acid, 5‐isoasparagine] Oxytocin

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1-Mercaptoacetic Acid-4-β-alanine-oxytocin*

Cited by 3 publications

References 10 publications

Impact of the Merrifield solid phase method on the design and synthesis of selective agonists and antagonists of oxytocin and vasopressin: A historical perspective

Impact of the Merrifield solid phase method on the design and synthesis of selective agonists and antagonists of oxytocin and vasopressin: A historical perspective

The Design of Peptide Hormone Analogs

STUDIES ON THE IMPORTANCE OF THE ASPARAGINE RESIDUE IN OXYTOCIN Synthesis and Some Pharmacological Properties of [1‐α‐Mercaptoacetic acid, 5‐isoasparagine] Oxytocin

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1-Mercaptoacetic Acid-4-β-alanine-oxytocin^*