Synthesis, structure and electrochemistry of ferrocene-peptide macrocycles.
Redox active cyclopeptides Fc[CSA]2 (5), Fc[Gly-CSA]2 (6), Fc[Ala-CSA]2 (7), Fc[Val-CSA](2) and Fc[Leu-CSA]2 (9) (CSA = cysteamine) which are formed by the reaction of ferrocenedicarboxylic acid with peptide cystamines at high dilutions. These systems exhibit H-bonding involving the amide NH in solution as shown by their temperature dependent NMR spectra. With the exception of 5, the ferrocene macrocycles display intramolecular N...O cross-ring H-bonding in the solid state involving the amino acids proximal to the ferrocene.
Chowdhury
Somenath
S
Department of Chemistry, University of Saskatchewan, 110 Science Place, Saskatoon, SK, Canada S7N 5C9.
Schatte
Gabriele
G
Kraatz
Heinz-Bernhard
HB
D000577:Amides / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry; D018360:Crystallography, X-Ray; D003538:Cystamine / Q000737:chemistry; D004563:Electrochemistry / Q000379:methods; D005296:Ferrous Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D000075163:Metallocenes; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry*; D013696:Temperature
D000577:Amides; D000596:Amino Acids; D005296:Ferrous Compounds; D006571:Heterocyclic Compounds; D000075163:Metallocenes; D010455:Peptides; D003538:Cystamine; C004998:ferrocene