Synthesis of phosphotyrosine‐containing peptides by the solid‐phase method
- 1 August 1993
- journal article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 42 (2) , 155-158
- https://doi.org/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).Keywords
This publication has 17 references indexed in Scilit:
- Preparation and use of Nα-fluorenylmethoxycarbonyl-O-dibenzylphosphono-L-tyrosine in continuous flow solid phase peptide synthesisJournal of the Chemical Society, Chemical Communications, 1991
- Synthesis of O-phosphotyrosine-containing peptides. 3. Synthesis of H-Pro-Tyr(P)-Val-OH via dimethyl phosphate protection and the use of improved deprotection proceduresThe Journal of Organic Chemistry, 1990
- Signal transduction by receptors with tyrosine kinase activityPublished by Elsevier ,1990
- Synthesis of O‐phosphonotyrosyl peptidesInternational Journal of Peptide and Protein Research, 1989
- Synthesis of phosphopeptides containing O‐phosphoserine or O‐phosphothreonineInternational Journal of Peptide and Protein Research, 1989
- Studies on peptides. CLXIV. Solution-phase synthesis of a 36-residue peptide amide corresponding to the entire amino acid sequence of chicken antral peptide.CHEMICAL & PHARMACEUTICAL BULLETIN, 1988
- Studies on peptides. CLXV. Combination of a new amide-precursor reagent and trimethylsilyl bromide deprotection for the 9-fluorenylmethyloxycarbonyl-based solid-phase synthesis of chicken antral peptide.CHEMICAL & PHARMACEUTICAL BULLETIN, 1988
- RECEPTORS FOR EPIDERMAL GROWTH FACTOR AND OTHER POLYPEPTIDE MITOGENSAnnual Review of Biochemistry, 1987
- Studies on peptides. CLV. Evaluation of trimethylsilyl bromide as a hard-acid deprotecting reagent in peptide synthesis.CHEMICAL & PHARMACEUTICAL BULLETIN, 1987
- Application of diphenylphosphinic carboxylic mixed anhydrides to peptide synthesisJournal of the Chemical Society, Perkin Transactions 1, 1985