Related Experiment Video
Updated: May 13, 2026

Synthesis of Protein Bioconjugates via Cysteine-maleimide Chemistry
Published on: July 20, 2016
Synthesis and characterization of water-soluble C60-peptide conjugates
Yue Ma1, Lorenzo Persi1, Yoko Yamakoshi1
1Department of Chemistry and Applied Biosciences, ETH Zürich, Vladimir-Prelog-Weg 3, 8093 Zürich, Switzerland.
Abstract:
With the aim of developing biocompatible and water-soluble C60 derivatives, three types of C60-peptide conjugates consisting of hydrophilic oligopeptide anchors (oligo-Lys, oligo-Glu, and oligo-Arg) were synthesized. A previously reported Prato reaction adduct of a biscarboxylic acid-substituted C60 derivative was subjected to a solid phase synthesis for amide formation with N-terminal amines of peptides on resin to successfully provide C60-peptide conjugates with one C60 and two peptide anchors as water-soluble moieties. Among three C60-peptide conjugates prepared, C60-oligo-Lys was soluble in water at neutral pH, and C60-oligo-Glu was soluble in buffer with a higher pH value, but C60-oligo-Arg was insoluble in water and most other solvents. C60-oligo-Lys and C60-oligo-Glu were characterized by 1H and 13C NMR. Photoinduced 1O2 generation was observed in the most soluble C60-oligo-Lys conjugate under visible light irradiation (527 nm) to show the potential of this highly water-soluble molecule in biological systems, for example, as a photosensitizer in photodynamic therapy.
Related Concept Videos
Carbon Skeletons
Newman Projections
The organic molecules rotate across the single bonds leading to numerous temporary three-dimensional structures of varying energy known as conformers.
Conformations of Cyclohexane
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal tetrahedral value,...
Chair Conformation of Cyclohexane
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this staggered...
C–C Bond Formation: Aldol Condensation Overview
Micelles

