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Synfacts 2006(6): 0621-0621  
DOI: 10.1055/s-2006-941803
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

A New Strategy Towards the Efficient Solid-Phase Synthesis of Cyclopeptides

Contributor(s): Yasuhiro Uozumi, Tomohiko Beppu
T. Berthelot, M. Gonçalves, G. Laïn, K. Estieu-Gionnet, G. Déléris*
Université Victor Segalen Bordeaux 2 and Université Bordeaux 1, Talence, France
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Publication History

Publication Date:
19 May 2006 (online)

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Significance

Cyclic peptide c(PHGRIK) was prepared by using Dmab as a protecting group. Thus, Fmoc-LysODmab, prepared from Fmoc-Lys(Boc)OH and DmabOH in the presence of DMAP and DCI (diisopropylcarbodiimide), was immobilized onto 2-chloro(chlorotrityl)resin to give resin 1. The resin-bound peptide 2 was prepared using 1 with five amino acids by automated peptide synthesizer. After the peptide synthesis, the Dmab group was removed using 2% hydrazine in DMF to give resin 3, which was reacted with PyBOP, HOBt and DIEA to afford resin-bound cyclic peptide 4. The desired cyclic peptide c(PHGRIK) was readily obtained in 25% yield via TFA-triisopropylsilan(TIS)-H2O-mediated cleavage from 4.