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Issue 4, 2007
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The synthesis of phosphopeptides via the Bpoc-based approach

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Abstract

The 2-(p-biphenylyl)-2-propyloxycarbonyl (Bpoc) group was examined as an Nα-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.

Graphical abstract: The synthesis of phosphopeptides via the Bpoc-based approach

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Article information


Submitted
04 Dec 2006
Accepted
06 Dec 2006
First published
12 Jan 2007

Org. Biomol. Chem., 2007,5, 664-670
Article type
Paper

The synthesis of phosphopeptides via the Bpoc-based approach

T. J. Attard, E. C. Reynolds and J. W. Perich, Org. Biomol. Chem., 2007, 5, 664
DOI: 10.1039/B617699M

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