Analogues of arginine vasopressin modified in the N-terminal part of the molecule with pipecolic acid isomers

  • Dariusz Sobolewski
  • Adam Prahl
  • Jiřina Slaninová
  • Bernard Lammek
Conference paper
Part of the Advances in Experimental Medicine and Biology book series (volume 611)


One of the most straightforward approaches for peptide modification is to introduce changes into the side chains of single amino acids. At this level, a multitude of possibilities for the synthesis of non-proteinogenic amino acids already exists, and useful preparative routes for the asymmetric synthesis of many derivatives have been developed. This strategy enabled incorporation of amino acids with side chains that do not or uncommonly occur naturally in peptides or proteins, with the aim to introduce special functional groups, either to restrict conformational flexibility of a peptide or to enhance its metabolic stability. Furthermore, D-configured amino acids, Nα-alkylated amino acids, or Cα-dialkylated amino acids can be employed.

We have designed ten new analogues of arginine vasopressin (AVP) modified in the N-terminal part of the molecule with pipecolic acid (Pip) isomers, a non-proteinogenic α-imino acid, also know as homoproline. Eight of the peptides were...


Carbonyl Oxygen Cys1 Residue Arginine Vasopressin Alkyl Side Chain Special Functional Group 
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Supported by grants 0066/H03/2006/30 and 1312/T09/2005/29 and by research project Z4055905.


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Copyright information

© Springer Science+Business Media, LLC 2009

Authors and Affiliations

  • Dariusz Sobolewski
    • 1
  • Adam Prahl
    • 1
  • Jiřina Slaninová
    • 2
  • Bernard Lammek
    • 1
  1. 1.Faculty of ChemistryUniversity of GdanskGdanskPoland
  2. 2.Institute of Organic Chemistry and BiochemistryAcademy of Sciences of the Czech RepublicPragueCzech Republic

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