Collect. Czech. Chem. Commun. 1980, 45, 435-441

The optically active 3-ferrocenylalanine and its application in peptide chemistry

Jan Pospíšeka, Štefan Tomab, Ivo Friča and Karel Bláhaa

a Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6
b Faculty of Sciences, Comenius Univeristy, 816 00 Bratislava


Racemic 3-ferrocenylalanine was resolved in enantiomers using brucine. The absolute configuration was estimated by ozonolytic degradation of the N-trifluoroacetyl derivative of the (-)-enantiomer yielding D-aspartic acid. Diastereoisomeric cyclo(D-ferrocenylalanyl-L-prolyl) and cyclo-(L-3-ferrocenylalanyl-L-prolyl) were synthesized using conventional methods of peptide synthesis. Circular dichroism spectra of these cyclodipeptides are discussed and compared with spectra of the corresponding diastereoisomeric cyclodipeptides containing phenylalanine.