Synthesis of protected L-4-[sulfono(difluoromethyl)]phenylalanine and its incorporation into a peptide

[GRAPHICS] A protected form of L-4-[sulfono(difluoromethyl)]phenylalanine (F(2)Smp), a novel non hydrolyzable phospho- and sulfotyrosine mimetic, was synthesized via electrophilic fluorination of a benzylic sulfonate followed by a Pd-catalyzed cross coupling reaction between the fluorinated sulfonate and the zincate of protected iodoalanine, F(2)Smp was incorporated into a peptide using solid-phase peptide synthesis techniques.