V. P. Kukhar

Convenient synthesis of optically active fluorocontaining amino acids

Abstract The development of new synthesis for fluorocontaining amino acids is of current bioorganic and biomedicinal interest. Polyfluoroalkylation of L -tyrosine and D -p-hydroxyphenylglycine derivatives, using difluorochloromethane or polyfluoroolefines, gives N -protected polyfluoroalkoxycontaining L - and D -amino acids, suitable for peptide synthesis as a carboxylic component. Free L - and D -fluorinated amino acids were obtained by removal of protecting groups. Optical activity of the starting material remains unchanged under polyfluoroalkylation conditions, except difluoromethylation of o -p-hydroxyphenylglycine, which proceeds with racemization. Synthesized compounds possesses 100% optical purity which was determined by HPLC.