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Pyruvoyl, a novel amino protecting group on the solid phase peptide synthesis and the peptide condensation reaction

✍ Scribed by Hidekazu Katayama; Takumi Utsumi; Chinatsu Ozawa; Yuko Nakahara; Hironobu Hojo; Yoshiaki Nakahara

Publisher: Elsevier Science
Year: 2009
Tongue: French
Weight: 247 KB
Volume: 50
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2008.12.005

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✦ Synopsis

In one of the peptide condensation methods termed thioester method, an amino protecting group is required in the lysine side chain. In this study, to investigate the efficiency of the pyruvoyl group as an amino protecting group, we synthesized N a -fluorenylmethoxycarbonyl (Fmoc)-N e -pyruvoyl-lysine and introduced it into peptides and glycopeptides by the ordinary Fmoc-based solid phase peptide synthesis. The pyruvoyl peptide could be condensed with a peptide thioester by the thioester method, and this protecting group was easily removed by o-phenylenediamine treatment without significant side reactions.

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