Synthesis and Application of Bis-Silylethyl-Derived Phosphate-Protected Fmoc-Phosphotyrosine Derivatives for Peptide Synthesis

Article abstract of DOI:10.1021/jo00101a029

Three Fmoc-phosphotyrosine derivatives with silylethyl-based phosphate protection were synthesized and evaluated for use in peptide synthesis.The stability of these derivatives toward piperidine/DMF (1:4) treatment and their cleavability with TFA solutions were examined.On the basis of these data, the bis<(methyldiphenylsilyl)ethyl>-protected Fmoc-phosphotyrosine derivative or Fmoc-Tyr(PO3MDPSE2)-OH, was shown to be the most suitable candidate for the production of phosphotyrosine peptides.The syntheses of phosphotyrosine peptides including one containing Met and Cys are described.