Synthesis and biological evaluation of gramicidin S dimers

Gijsbert M. Grotenbreg; Martin D. Witte; Peter A. V. van Hooft; Emile Spalburg; Philipp Reiß; Daan Noort; Albert J. de Neeling; Ulrich Koert; Gijsbert A. van der Marel; Herman S. Overkleeft; Mark Overhand

doi:10.1039/B414618B

Synthesis and biological evaluation of gramicidin S dimers†

Gijsbert M. Grotenbreg,^a Martin D. Witte,^a Peter A. V. van Hooft,^b Emile Spalburg,^c Philipp Reiß,^d Daan Noort,^b Albert J. de Neeling,^c Ulrich Koert,^d Gijsbert A. van der Marel,^a Herman S. Overkleeft*^a and Mark Overhand*^a

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* Corresponding authors

^a Leiden Institute of Chemistry, Gorlaeus Laboratories, P. O. Box 9502, RA Leiden, The Netherlands
E-mail: overhand@chem.leidenuniv.nl
Fax: +31(0)71-5274307

^b TNO Prins Maurits Laboratory, P.O. Box 45, AA Rijswijk, The Netherlands

^c National Institute of Public Health and the Environment, Research Laboratory for Infectious Diseases, P.O. Box 1, BA Bilthoven, The Netherlands

^d Philipps-Universität Marburg, Fachbereich Chemie, Hans-Meerwein-Strasse, Marburg, Germany

Abstract

The design and synthesis of analogues of the cyclic β-sheet peptide gramicidin S (GS), having additional functionalities in their turn regions, is reported. The monomeric GS analogues were transformed into dimers and their activities towards biological membranes, through antimicriobial and hemolytic assays, were evaluated. Finally, conductivity measurements have been performed to elucidate ion channel forming properties.

Organic & Biomolecular Chemistry

Synthesis and biological evaluation of gramicidin S dimers†

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Synthesis and biological evaluation of gramicidin S dimers

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