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RESEARCH PRODUCT
C2-Symmetric Ferrocene-Bis(ureido)peptides : Synthesis, Conformation and Solid-State Structure
Vladimir RapićJasmina LapićMario CetinaKatja HeinzeSenka Djakovićsubject
chemistry.chemical_classificationAlanineCircular dichroismStereochemistryHydrogen bondPeptideInorganic Chemistrychemistry.chemical_compoundDicarboxylic acidFerrocenechemistryIntramolecular forceconformation analysis; density functional calculations; hydrogen bonds; metallocenes; peptidesProtein secondary structuredescription
The extension of peptide derivatives of ferrocene-1,1'-dicarboxylic acid by formal insertion of NH units between ferrocene and peptide strands results in ferrocene-bis(ureido)-peptides. Experimentally, alanine and dialanine methyl esters were attached to the 1- and 1'-position of 1,1'-diiso-cyanoferrocene to give the corresponding bis(ureido)peptide derivatives 3 and 4. The conformation of 3 has been determined in the solid state by X-ray crystallography. In solution the preferred conformation of 3 and 4 has been elucidated by NMR, IR and CD spectroscopy in concert with DFT calculations. The secondary structure of ferrocene―bis(ureido)peptides 3 and 4 is determined by double bifurcated intramolecular hydrogen bonds (IHBs). The different stability of the secondary structures of 3 and 4 is due to different types of IHBs.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2009-12-21 |