N,N'-dialkyldiamide-type phosphate protecting groups for Fmoc synthesis of phosphotyrosine-containing peptides

Article abstract of DOI:10.1016/0040-4039(96)01077-5

Z-Tyr[P(O)(NHR)₂]-OBzl (R=n-Pr and i-Pr) were obtained by reactions of Z-Tyr-OBzl, lithiated with LDA, with N,N -dipropyl- or diisopropyl- phosphorodiamidic chloride. Fmoc derivatives, Fmoc-Tyr][P(O)(NHR)₂]-OH, were obtained from them as stable crystals. The P-N bonds are stable toward 20% piperidine in DMF and were cleaved completely with 95% trifluoroacetic acid.