title: N-methyl-phenacyloxycarbamidomethyl (Pocam) group: a novel thiol protecting 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.
authors.affiliation: Department of Applied Biochemistry, Faculty of Engineering, Tokai University, Hiratsuka, Kanagawa 259-1292, Japan. katay@tokai-u.jp
authors.forename: Hidekazu
authors.initials: H
authors.lastname: Katayama
authors.forename: Yoshiaki
authors.initials: Y
authors.lastname: Nakahara
authors.forename: Hironobu
authors.initials: H
authors.lastname: Hojo
mesh_terms: D000818:Animals; D001386:Azides / Q000737:chemistry; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D056148:Chromatography, Reverse-Phase; D003545:Cysteine / Q000737:chemistry*; D006801:Humans; D007202:Indicators and Reagents / Q000138:chemical synthesis*; D008239:Lysine / Q000737:chemistry*; D010455:Peptides / Q000032:analysis / Q000138:chemical synthesis*; D060327:Solid-Phase Synthesis Techniques / Q000379:methods*; D015032:Zinc / Q000737:chemistry
chemical_list: D001386:Azides; D007202:Indicators and Reagents; D010455:Peptides; D015032:Zinc; D008239:Lysine; D003545:Cysteine