Issue 12, 2011

N-Methyl-phenacyloxycarbamidomethyl (Pocam) group: a novel thiolprotecting group for solid-phase peptide synthesis and peptide condensation reactions

Abstract

In the so-called thioester method for the condensation of peptide segments, protecting groups for amino and thiol groups are required for chemoselective ligation. In this study, we developed a novel thiol protecting group, N-methyl-phenacyloxycarbamidomethyl (Pocam). We used it for protection of cysteine side chains, and synthesized Pocam-containing peptides and peptide thioesters. These were condensed by the thioester method. After the condensation reaction, Pocam groups were cleaved by Zn/AcOH treatment. At the same time, the azido group, which was used for the protection of lysine side chains, was also converted to an amino group, demonstrating that this protecting group strategy simplified the deprotecting reaction after the peptide condensation reaction to only one step.

Graphical abstract: N-Methyl-phenacyloxycarbamidomethyl (Pocam) group: a novel thiol protecting group for solid-phase peptide synthesis and peptide condensation reactions

Supplementary files

Article information

Article type
Paper
Submitted
17 Feb 2011
Accepted
04 Apr 2011
First published
03 May 2011

Org. Biomol. Chem., 2011,9, 4653-4661

N-Methyl-phenacyloxycarbamidomethyl (Pocam) group: a novel thiol protecting group for solid-phase peptide synthesis and peptide condensation reactions

H. Katayama, Y. Nakahara and H. Hojo, Org. Biomol. Chem., 2011, 9, 4653 DOI: 10.1039/C1OB05253E

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