6533b86cfe1ef96bd12c80e4
RESEARCH PRODUCT
Ferrocenyl-Labeled Sugar Amino Acids: Conformation and Properties
Christoph FörsterKatja HeinzeLidija BarišićVladimir RapićMonika Kovačevićsubject
chemistry.chemical_classificationHydrogen bondOrganic ChemistryMedicinal chemistryRedoxAmino acidInorganic Chemistrychemistry.chemical_compoundFerrocenechemistryconformational analysis; hydrogen bonds; metallocenes; redox chemistry; sugar amino acidsAmideLipophilicityOrganic chemistryMoietyHydroxymethylPhysical and Theoretical Chemistrydescription
Novel organometallic sugar amino acid conjugates 1–5 have been prepared by amide coupling of O-protected N-acetylmuramic acid and iso-muramic acid (2-[3-amino-2, 5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxypropanoic acid) with 1-aminoferrocene, 1-aminoferrocene-1′-carboxylic acid (H-Fca-OH), or 1, 1′-diaminoferrocene, respectively. The influence of the ferrocenyl moiety and presence of additional remote potential hydrogen atom acceptors and donors at the ferrocenyl core on the conformation and lipophilicity is investigated by TLC, IR, NMR, and CD spectroscopic methods augmented by density functional calculations. Furthermore, the redox potential of the ferrocene/ferrocenium couple is tuned by the electron-withdrawing and -donating nature of the substituents at the ferrocenyl label.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2012-04-27 |