Fullerene-Derivatized Amino Acids: Synthesis, Characterization, Antioxidant Properties, and Solid-Phase Peptide Synthesis

• Published in: Chemistry : a European journal Vol. 13; no. 9; pp. 2530 - 2545
• Main Authors: Yang, Jianzhong, Alemany, Lawrence B., Driver, Jonathan, Hartgerink, Jeffrey D., Barron, Andrew R.
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01-01-2007; WILEY‐VCH Verlag
• Subjects: amino acids; Amino Acids - chemical synthesis; Amino Acids - chemistry; Amino Acids - pharmacology; antioxidant; Antioxidants - chemical synthesis; Antioxidants - chemistry; Antioxidants - pharmacology; fullerenes; Fullerenes - chemistry; Magnetic Resonance Spectroscopy; Microscopy, Electron, Transmission; peptides; Peptides - chemical synthesis; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; Spectrophotometry, Ultraviolet
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.200601186

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.
Ball‐and‐chain amino acids: Fullerene‐substituted phenylalanine (Baa) and lysine derivatives are prepared by the condensation of 1,2‐(4′‐oxocyclohexano)fullerene with the appropriate (4‐amino)phenylalanine and lysine. 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.