SYNTHESIS AND APPLICATION OF BIS-SILYLETHYL-DERIVED PHOSPHATE-PROTECTED FMOC-PHOSPHOTYROSINE DERIVATIVES FOR PEPTIDE-SYNTHESIS

Three Fmoc-phosphotyrosine derivatives with silylethyl-based phosphate protection were synthesized and evaluated for use in peptide synthesi s. The stability of these derivatives toward piperidine/DMF (1:4) trea tment and their cleavability with TFA solutions were examined. On the basis of these data, the bis[(methyldiphenylsilyl)ethyl]-protected Fmo c-phosphotyrosine derivative or Fmoc-Tyr(PO(3)MDPSE(2))-OH, was shown to be the most suitable candidate for the production of phosphotyrosin e peptides. The syntheses of phosphotyrosine peptides including one co ntaining Met and Cys are described.