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

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

Research output: Contribution to journalArticle

50 Citations (Scopus)

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
Externally publishedYes

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amino acids
Amino Acids
X ray crystallography
X Ray Crystallography
synthesis
crystallography
Nuclear magnetic resonance
nuclear magnetic resonance
Chirality
alanine
chirality
Alanine
peptides
x rays
Magnetic Resonance Spectroscopy
Spectroscopy
Derivatives
solid state
Peptides
rings

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)
  • Chemistry(all)

Cite this

Amino acid conjugates of 1,1′-diaminoferrocene. Synthesis and chiral organization. / Chowdhury, Somenath; Mahmoud, Khaled; Schatte, Gabriele; Kraatz, Heinz Bernhard.

In: Organic and Biomolecular Chemistry, Vol. 3, No. 16, 21.08.2005, p. 3018-3023.

Research output: Contribution to journalArticle

Chowdhury, Somenath ; Mahmoud, Khaled ; Schatte, Gabriele ; Kraatz, Heinz Bernhard. / Amino acid conjugates of 1,1′-diaminoferrocene. Synthesis and chiral organization. In: Organic and Biomolecular Chemistry. 2005 ; Vol. 3, No. 16. pp. 3018-3023.
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