Bisphosphine-functionalized cyclic decapeptides based on the natural product gramicidin s: A potential scaffold for transition-metal coordination

Sebastian Burck, Sander G.A. Van Assema, Bas Lastdrager, J. Chris Slootweg, Andreas W. Ehlers, José M. Otero, Bruno Dacunha-Marinho, Antonio L. Llamas-Saiz, Mark Overhand, Mark J. Van Raaij, Koop Lammertsma

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)


The natural product Gramicidin S is a promising scaffold for novel oligopeptide-based bisphosphine ligands, combining the advantageous rigid chiral backbone with the close proximity of phosphine substituents. The required unnatural, phosphine-containing, amino acid building blocks were synthesized by means of a novel protocol that involves the enantioselective alkylation of a chiral nickel Schiff base template. Three Ni complexes were prepared with different alkyl chains between the phosphine group and the α-carbon atom of the incorporated glycine; the absolute stereochemistry of two of them was determined by single-crystal X-ray structure analysis. By detaching the template, enantiopure L-phosphine amino acids resulted enabling the solid-phase, stepwise construction of a linear sequence of the phosphine-modified oligopeptides. On cyclization three bisphosphine-substituted Gramicidin S analogues resulted, differing only in the size and shape of the linkage between the phosphine groups and the oligopeptides backbone. Their crystal structures suggest these species to have potential as chelating ligands.

Original languageEnglish
Pages (from-to)8134-8145
Number of pages12
JournalChemistry - A European Journal
Issue number33
Publication statusPublished - 17 Aug 2009
Externally publishedYes


  • Aniino acids
  • Pcplides
  • Phosphancs
  • Solid-phase synthesis
  • X-ray diffraction

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Organic Chemistry


Dive into the research topics of 'Bisphosphine-functionalized cyclic decapeptides based on the natural product gramicidin s: A potential scaffold for transition-metal coordination'. Together they form a unique fingerprint.

Cite this