Analogs of oxytocin containing a pseudopeptide Leu‐Gly bond of cis and trans configuration

MICHAL LEBL, JIŘINA SLANINOVÁ, RODNEY L. JOHNSON

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21 Scopus citations

Abstract

Analogs of deamino‐oxytocin wherein the Leu‐Gly peptide bond has been replaced by a tetrazole moiety or by a double bond of trans configuration were synthesized and their biological activities evaluated. Trans double bond was found to be the most appropriate substitution for the amide bond (uterotonic activity 24% of the deamino‐oxytocin). In the case of all three analogs low but prolonged galactogogic activity was found and the ratio of uterotonic in vitro and in vivo activity was surprisingly high (ranging from 4.5 to 20).

Original languageEnglish (US)
Pages (from-to)16-21
Number of pages6
JournalInternational Journal of Peptide and Protein Research
Volume33
Issue number1
DOIs
StatePublished - Jan 1989

Keywords

  • modified peptide bonds
  • oxytocin analogs
  • tetrazole replacement
  • trans substituted double bond

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