TY - JOUR
AU - Barron, Andrew R.
AB - A series of [60]fullerene‐substituted phenylalanine (Baa) and lysine derivatives have been prepared by the condensation of 1,2‐(4′‐oxocyclohexano)fullerene with the appropriately protected (4‐amino)phenylalanine and lysine, respectively. Conversion of the imine to the corresponding amine is achieved by di‐acid catalyzed hydroboration. The reduction of the imine is not accompanied by hydroboration of the fullerene cage. The [70]fullerene phenylalanine derivative has also been prepared as have the di‐amino acid derivatives. The compounds were characterized by MALDI‐TOF mass spectrometry, UV/Vis spectroscopy, and cyclic voltammetry. 1H and 13C NMR spectroscopy allowed the observation of diastereomers. Fullerene‐substituted peptides may be synthesized on relatively large scale by solid‐phase peptide synthesis. The presence of the C60‐substituted amino acid in a peptide has a significant effect on the secondary structures and self‐assembly properties of peptides as compared to the native peptide. The antioxidant assay of Baa and a Baa‐derived anionic peptide was determined to be significantly more potent than Trolox.
TI - Fullerene‐Derivatized Amino Acids: Synthesis, Characterization, Antioxidant Properties, and Solid‐Phase Peptide Synthesis
JF - Chemistry - A European Journal
DO - 10.1002/chem.200601186
DA - 2008-04-16
UR - https://www.deepdyve.com/lp/wiley/fullerene-derivatized-amino-acids-synthesis-characterization-Ao5KOq19yY
SP - 2530
EP - 2545
VL - 13
IS - 9
DP - DeepDyve
ER -