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Fmoc Solid-Phase Synthesis of C-Terminal Peptide Thioesters by Formation of a Backbone Pyroglutamyl Imide Moiety


  • A grant from the Danish Council for Strategic Research to K.J.J. is gratefully acknowledged. Fmoc=9-fluorenylmethoxycarbonyl.


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Activating an inactive bond: A new concept in synthetic peptide chemistry, backbone amide activation, proceeds through the selective conversion of a backbone amide into an imide, followed by nucleophilic acyl displacement (see scheme; Boc=tert-butoxycarbonyl, Pg=protecting group). This methodology represents a new approach to solid-phase synthesis of C-terminal peptide thioesters, and may become a general tool for the synthesis of peptide thioesters.