Synthesis of Tyr(P)-containing peptides via ‘on-line’ phosphorylation of the tyrosine residue on the solid phase

✍ Scribed by John W. Perich

• Book ID: 104634804
• Publisher: Springer Netherlands
• Year: 1996
• Tongue: English
• Weight: 418 KB
• Volume: 3
• Category: Article
• ISSN: 1573-3149
• DOI: 10.1007/bf00132975

✦ Synopsis

A novel method for the efficient synthesis of Tyr(P)-containing peptides is described by the 'phosphite-triester' phosphorylation of the tyrosine residue after its incorporation into the peptide chain. In this approach, the peptide resin is assembled by Fmoc solid-phase peptide synthesis (PyBOP ® couplings) with the tyrosine residue incorporated as Fmoc-Tyr-OH. The N-terminal tyrosine peptide resin is then phosphorylated with di-t-butyl N,N-diethylphosphoramidite/1H-tetrazole and the intermediate di-t-butyl phosphite triester is oxidised by treatment with m-chloroperoxybenzoic acid. Peptide synthesis is then continued under usual conditions and the peptide resin is deprotected by acidolytic treatment. The improved efficiency of the 'on-line' phosphorylation approach is demonstrated through the syntheses of IVPNY(P)VEE and the Fe'/receptor peptide, EAENTITY(P)SLLKHPEAL, in both good yield and purity.