6533b85cfe1ef96bd12bc87b

RESEARCH PRODUCT

Conformational stability of oligoferrocene oligoamide foldamers

Daniel SieblerDaniel SieblerKatja Heinze

subject

chemistry.chemical_classificationHydrogen010405 organic chemistryDimethyl sulfoxideStereochemistryHydrogen bondCarboxylic acidOrganic ChemistryFoldamerchemistry.chemical_element010402 general chemistry01 natural sciencesBiochemistry0104 chemical sciencesAmino acidInorganic Chemistrychemistry.chemical_compoundCrystallographychemistryFerroceneMaterials ChemistryPhysical and Theoretical ChemistryProtein secondary structure

description

Abstract Organometallic oligoamides built from three to four ferrocene amino acid units ( H-Fca-OH , 1-amino-1′-ferrocene carboxylic acid) fold into hydrogen bonded secondary structures featuring eight-membered rings by cooperative hydrogen bonds. NMR studies and DFT calculations (CAM-B3LYP, LANL2DZ, IEFPCM (THF)) reveal that the organometallic zigzag foldamer structures are highly resistant toward denaturation by hydrogen bond acceptors such as dimethyl sulfoxide and 2,4-lutidine. Replacing one ferrocene amino acid unit by the organic α -amino acid glycine at the C -terminal end (Fca → Gly) significantly destabilizes the secondary zigzag structure facilitating denaturation by DMSO. Highly stabilized ordered poly(Fca) architectures are very attractive for future applications of switchable hydrogen-bonded redox-active materials.

yearjournalcountryeditionlanguage
2016-10-01Journal of Organometallic Chemistry
https://doi.org/10.1016/j.jorganchem.2016.02.032