Amino acid conjugates of 1,1'-diaminoferrocene. Synthesis and chiral organization.
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.
Chowdhury
Somenath
S
Department of Chemistry, University of Saskatchewan, Saskatoon, SK S7N 5C9, Canada.
Mahmoud
Khaled A
KA
Schatte
Gabriele
G
Kraatz
Heinz-Bernhard
HB
D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry*; D018360:Crystallography, X-Ray; D005296:Ferrous Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D000075163:Metallocenes; D011487:Protein Conformation
D000596:Amino Acids; D005296:Ferrous Compounds; D000075163:Metallocenes; C004998:ferrocene