SYNTHESIS, CHIROPTICAL PROPERTIES, AND CONFIGURATIONAL ASSIGNMENT OF FULLEROPROLINE DERIVATIVES AND PEPTIDES

1,3-Dipolar cycloaddition of azomethine ylides to C-60 leads to fuller oproline derivatives, in which a proline ring is fused on a 6,6-ring j unction of the fullerene spheroid. This unnatural amino acid can be ma nipulated under standard coupling conditions to afford fulleroproline- containing peptides, All optically active fulleroproline derivatives a nd peptides display a characteristic maximum at 428 Mn in CD spectra, which is diagnostic for the assignment of the absolute configuration o f the C-alpha atom of the proline ring. Calculation of the CD spectra confirm the configurational assignment.