These tools will no longer be maintained as of December 31, 2024. Archived website can be found here. PubMed4Hh GitHub repository can be found here. Contact NLM Customer Service if you have questions.


Pubmed for Handhelds

PUBMED FOR HANDHELDS

Search MEDLINE/PubMed

  • Title: Synthesis of biologically active dicarba analogues of the peptide hormone oxytocin using ring-closing metathesis.
    Author: Stymiest JL, Mitchell BF, Wong S, Vederas JC.
    Journal: Org Lett; 2003 Jan 09; 5(1):47-9. PubMed ID: 12509887.
    Abstract:
    Facile synthesis of cis and trans olefinic analogues of oxytocin 1 that have carbon in place of sulfur is achieved via ring-closing metathesis (RCM) on a resin-bound linear precursor peptide. Hydrogenation of the cis olefin, 3, proceeds selectively to generate the previously reported saturated derivative 5. Biological testing on rat uterus strips shows that cis compound 3 has an EC50 value of 38 ng/mL (EC50 for oxytocin is 2.7 ng/mL) whereas 5 and trans olefin 4 are less active. [reaction--see text]
    [Abstract] [Full Text] [Related] [New Search]