Stereospecific synthesis of 4-carboxyphenylalanine and derivatives for use in Fmoc-based solid-phase peptide synthesis

Article abstract of DOI:10.1016/S0040-4039(96)01490-6

Starting from N(α)-benzyloxycarbonyl-L-tyrosine(O-triflate) benzyl ester, we have prepared enantiomerically pure 4-carboxyphenylalanine and 4-methoxycarbonylphenylalanine derivatives using palladium (0) catalyzed carbonylation reactions. These unnatural amino acids were suitably protected and were used in solid-phase peptide synthesis using the Fmoc/t-butyl approach.