Synthesis and characterization of new ferrocene peptide conjugates.
Three classes of diamine linked ferrocene (Fc)-conjugates were prepared and their properties were investigates in solution and the solid state: (a) acyclic diamine-linked 1,n'-Fc conjugates, (b) acyclic diamine-linked 1,n'-Fc peptide conjugates, and (c) cyclic 1,n'-Fc-peptide diamine conjugates. In all cases, the synthetic procedure started from 1,1'-ferrocenecarboxylic acid methyl ester or 1,1'-ferrocene dicarboxylic acid or their amino acid conjugates followed by coupling with diaminoalkanes. The resulting conjugates exhibit H-bonding as is evident by temperature and, in some cases, concentration-dependent NMR shifts and in the solid-state structure of one of the conjugates. Our studies show that the structural properties of Fc-diamine-linked systems are different from those of the related cystamine conjugates, presumably due to the enhanced flexibility of the conjugates.
Drexler
Cailin
C
Department of Chemistry, University of Western Ontario, London, ON, Canada.
Milne
Mark
M
Morgan
Erin
E
Jennings
Michael
M
Kraatz
H-B
HB
D018360:Crystallography, X-Ray; D003959:Diamines / Q000138:chemical synthesis / Q000737:chemistry*; D004563:Electrochemistry; D005296:Ferrous Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D047028:Macrocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D000075163:Metallocenes; D008958:Models, Molecular; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry*
D003959:Diamines; D005296:Ferrous Compounds; D047028:Macrocyclic Compounds; D000075163:Metallocenes; D010455:Peptides; C004998:ferrocene