Stereoselective formation of chiral metallopeptides

Gustavo Rama, Ana Ardá, Jean Didier Maréchal, Ilaria Gamba, Hitoshi Ishida, Jesús Jiménez-Barbero, M. Eugenio Vázquez, M. Vázquez López

Research output: Contribution to journalArticleResearchpeer-review

24 Citations (Scopus)

Abstract

Playing into our hands: The achiral bipyridine amino acid fluorenylmethyloxycarbonyl 5-amino-3-oxapentanoic acid (Fmoc-O1PenBpy-OH) has been used for the solid-phase synthesis of metallopeptides. Circular dichroism, molecular modeling, and NMR spectroscopic studies show that the chirality of the resulting metal complexes in aqueous solution is determined, and can thus be controlled, by the stereochemistry of one proline residue in the loop between the two coordinating O1PenBpy residues. © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Original languageEnglish
Pages (from-to)7030-7035
JournalChemistry - A European Journal
Volume18
Issue number23
DOIs
Publication statusPublished - 4 Jun 2012

Keywords

  • chirality
  • ligand effects
  • metallopeptides
  • molecular modeling
  • NMR spectroscopy
  • peptides

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