Solid‐phase synthesis of peptides containing phosphoserine using phosphate tert.‐butyl protecting group*
- 1 September 1990
- journal article
- research article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 36 (3) , 275-280
- https://doi.org/10.1111/j.1399-3011.1990.tb00978.x
Abstract
In this paper, we report the solid‐phase synthesis of peptides containing O‐phosphonoserine using BOP as coupling reagent. Commercially available Fmoc amino‐acids linked to p‐alkoxybenzyl resin were used in the first step and Alloc amino acids in the following. Alloc group was removed by catalytic hydrostannolytic cleavage. Acid‐labile side‐chain protecting groups (including phosphate residue) were used. Thus, both removal of side‐chain protecting groups and cleavage of the phosphopeptide from the resin were achieved in one step by treatment with TFA. Alloc serine was phosphorylated by the phosphoramidite method. This strategy enables the preparation of peptides with selectively phosphorylated residue and overcomes problems due to repetitive treatments with TFA and final cleavage with HF.Keywords
This publication has 36 references indexed in Scilit:
- Synthesis of O-phosphotyrosine-containing peptides. 1. Synthesis of PTyr-Leu-Gly via benzyl phosphate protectionThe Journal of Organic Chemistry, 1989
- Studies of phosphorylated sites in proteins using proton-phosphorus-31 two-dimensional NMR: further evidence for a phosphodiester link between a seryl and a threonyl residue in Azotobacter flavodoxinJournal of the American Chemical Society, 1988
- Synthesis of phosphopeptides: A simple phosphorylation procedure for serine and threonineRecueil des Travaux Chimiques des Pays-Bas, 1987
- An Efficient One-Pot Synthesis ofN-Protected α-Amino-β-dialkoxyphosphinyloxy(diphenoxyphosphinyloxy)-carboxylic Acids (Phosphate-Group Esters ofO-PhosphorylatedN-Protected α-Amino-β-hydroxyamino Acids)Synthesis, 1986
- Amino acid sequence round the site of phosphorylation in isocitrate dehydrogenase from Escherichia coli ML308FEBS Letters, 1984
- Synthesis of the Phosphonic Acid Analog of SerineSynthesis, 1984
- Preparation of Nα-(t-Butoxycarbonyl)-O-(dibenzylphosphono)-L-serineAustralian Journal of Chemistry, 1984
- p-Alkoxybenzyl Alcohol Resin and p-Alkoxybenzyloxycarbonylhydrazide Resin for Solid Phase Synthesis of Protected Peptide FragmentsJournal of the American Chemical Society, 1973
- 1007. Anionic polymerization of styrene: conductivity measurementsJournal of the Chemical Society, 1960
- Amino Acid Derivatives. I. Carboallyloxy Derivatives of α-Amino Acids1,2Journal of the American Chemical Society, 1950