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C 2 ‐Symmetric Ferrocene–Bis(ureido)peptides: Synthesis, Conformation and Solid‐State Structure
Author(s) -
Lapić Jasmina,
Djaković Senka,
Cetina Mario,
Heinze Katja,
Rapić Vladimir
Publication year - 2010
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.200900679
Subject(s) - chemistry , ferrocene , intramolecular force , peptide , hydrogen bond , stereochemistry , solid state , nuclear magnetic resonance spectroscopy , crystallography , alanine , amino acid , molecule , organic chemistry , electrochemistry , biochemistry , electrode
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′‐diisocyanoferrocene 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.