O-(carboxydifluoromethyl)- L-tyrosine: Design and synthesis of a novel non phosphorous- containing phosphotyrosine isostere

Article abstract of DOI:10.1016/S0040-4020(98)00192-6

O-(Carboxydifluoromethyl)-L-tyrosine 1 was designed as a non phosphorous-containing phosphotyrosine isostere. A synthesis leading to the racemic as well as a stereoselective preparation of the L-configurated amino acid is described. Conversion into the respective Fmoc derivatives DL-2 and L-2 afforded building blocks suitably protected for solid-phase peptide synthesis.