Synthesis of phosphotyrosine-containing peptides by the solid-phase method. A re-examination of the use of Boc-Tyr(PO3Bzl2)-OH.
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).
Tian
Z
Z
Department of Biochemistry and Molecular Biology, Indiana University School of Medicine, Indianapolis.
Gu
C
C
Roeske
R W
RW
Zhou
M
M
Van Etten
R L
RL
D000595:Amino Acid Sequence; D001457:Anion Exchange Protein 1, Erythrocyte / Q000737:chemistry*; D004126:Dimethylformamide / Q000737:chemistry; D008752:Methylene Chloride / Q000737:chemistry; D008969:Molecular Sequence Data; D010446:Peptide Fragments / Q000737:chemistry*; D010748:Phosphopeptides / Q000138:chemical synthesis*; D019000:Phosphotyrosine; D014443:Tyrosine / Q000031:analogs & derivatives* / Q000737:chemistry
D001457:Anion Exchange Protein 1, Erythrocyte; D010446:Peptide Fragments; D010748:Phosphopeptides; D019000:Phosphotyrosine; D014443:Tyrosine; D008752:Methylene Chloride; D004126:Dimethylformamide