Synthesis of phosphotyrosine-containing peptides by the solid-phase method. A re-examination of the use of Boc-Tyr(PO3Bzl2)-OH

Int J Pept Protein Res. 1993 Aug;42(2):155-8. doi: 10.1111/j.1399-3011.1993.tb00491.x.

Abstract

A practical and convenient procedure for making phosphotyrosine-containing peptides by the solid-phase method was developed. Phosphotyrosine was incorporated via Boc-Tyr(PO3Bzl2)-OH. The completed peptide was cleaved from the solid support by treatment with 1 M TMSBr-thioanisole-TFA. By gel-phase 31P-NMR spectroscopy we found that one of the benzyl protecting groups on phosphate was completely removed by two consecutive runs of Boc deprotection with 50% TFA-DCM. However, the other benzyl group remained intact throughout the synthesis (35 cycles).

MeSH terms

  • Amino Acid Sequence
  • Anion Exchange Protein 1, Erythrocyte / chemistry*
  • Dimethylformamide / chemistry
  • Methylene Chloride / chemistry
  • Molecular Sequence Data
  • Peptide Fragments / chemistry*
  • Phosphopeptides / chemical synthesis*
  • Phosphotyrosine
  • Tyrosine / analogs & derivatives*
  • Tyrosine / chemistry

Substances

  • Anion Exchange Protein 1, Erythrocyte
  • Peptide Fragments
  • Phosphopeptides
  • Phosphotyrosine
  • Tyrosine
  • Methylene Chloride
  • Dimethylformamide