Journal article

The synthesis of phosphopeptides via the Bpoc-based approach

Troy J Attard, Eric C Reynolds, John W Perich

ORGANIC & BIOMOLECULAR CHEMISTRY | ROYAL SOC CHEMISTRY | Published : 2007

Abstract

The 2-(p-biphenylyl)-2-propyloxycarbonyl (Bpoc) group was examined as an N(alpha)-protecting group in the stepwise assembly of the MAP Kinase ERK2 [178-188; Thr(P)(183), Tyr(P)(185)] peptide. The mild acid deprotection of the Bpoc group permitted (i) incorporation of a fully protected phosphothreonyl derivative and (ii) a TFA-based final cleavage step. The first five C-terminal residues (184-188) were incorporated in the Fmoc mode of peptide synthesis, with all subsequent amino acids coupled as their Bpoc-Xxx-OH derivatives. The target product was obtained in high purity and yield, indicating that a Bpoc-based approach to phosphopeptide synthesis was compatible with both the acid-labile side..

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