Vasopressin and oxytocin analogs with interchanged sequence of amino acids in positions 7 and 8. synthesis and biological effects
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Published:1981
Issue:9
Volume:46
Page:2136-2139
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ISSN:0010-0765
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Container-title:Collection of Czechoslovak Chemical Communications
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language:en
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Short-container-title:Collect. Czech. Chem. Commun.
Author:
Bláha Ivo,Krchňák Viktor,Zaoral Milan
Abstract
p-Toluenesulfonyl-S-benzylcysteinyl-tyrosyl-phenylalanyl-glutaminyl-asparaginyl-S-benzylcysteinyl-NG-p-toluenesulfanylarginyl-prolyl-glycineamide (I) and S-benzylcysteinyl-tyrosyl-isoleucyl-glutaminyl-asparaginyl-S-benzylcysteinyl-leucyl-prolyl-glycine amide (III) were prepared by solid phase synthesis. After removal of the protecting groups, closure of the disulfide ring, and purification by continuous free-flow electrophoresis [arginine7, proline8]vasopressin (II) and [leucine7, proline8]oxytocin (IV) were obtained. The antidiuretic effect of II is markedly higher than its pressor effect; IV possesses c. 6% of the uterotonic and c. 10% of the galactogogous effect of oxytocin.
Publisher
Institute of Organic Chemistry & Biochemistry
Subject
General Chemistry
Cited by
2 articles.
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1. Sequence Modification in Neurohypophyseal Hormones;Collection of Czechoslovak Chemical Communications;1992
2. Structure–Activity Relationships of Neurohypophyseal Peptides;Chemistry, Biology, and Medicine of Neurohypophyseal Hormones and their Analogs;1987