Amino acid conjugates of 1,1′-diaminoferrocene. Synthesis and chiral organization

Somenath Chowdhury, Khaled A. Mahmoud, Gabriele Schatte, Heinz Bernhard Kraatz

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Abstract

1,1′-Bis(tert-butoxycarbonylamino)ferrocene (6), a protected derivative of 1,1′-diaminoferrocene, has been synthesized by a very convenient method and serves as a synthon for 1,1′-diaminoferrocene. Its structure in solid state and in solution has been studied by NMR and X-ray crystallography. 1,1′-Bis(tert-butoxycarbonylamino)ferrocene serves as starting material for the synthesis of amino acid conjugates of L- and D-alanine. The structures of these bioconjugates have been studied by NMR and CD spectroscopy and X-ray crystallography and reveal that the chiral organization of the podant amino acid chains is controlled by the chirality of the attached amino acid. The substituents engage in strong intramolecular H-bonding generating 14-membered H-bonded rings, a motif previously unrealized in ferrocene-amino acid and peptide conjugates.

Original languageEnglish
Pages (from-to)3018-3023
Number of pages6
JournalOrganic and Biomolecular Chemistry
Volume3
Issue number16
DOIs
Publication statusPublished - 21 Aug 2005

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ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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