The synthesis of phosphopeptides via the Bpoc-based approach.
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 chain protecting groups employed and Hmp-Wang resin.
Attard
Troy J
TJ
Department of Chemistry, University of Melbourne, Victoria, Australia. jattard@unimelb.au
Reynolds
Eric C
EC
Perich
John W
JW
D001713:Biphenyl Compounds / Q000737:chemistry*; D015394:Molecular Structure; D010748:Phosphopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D013997:Time Factors
C519292:(4-biphenylyl)-2-propyloxycarbonylphenyl carbonate; D001713:Biphenyl Compounds; D010748:Phosphopeptides