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A water soluble Cu(I)-NHC for CuAAC ligation of unprotected peptides under open air conditions

Christelle Gaulier1, Audrey Hospital, Bertrand Legeret

  • 1Institut de Chimie de Clermont-Ferrand, CNRS UMR 6296, Clermont-Université, 24 Ave des Landais, F-63177 Aubière, France.

Chemical Communications (Cambridge, England)
|March 17, 2012
PubMed

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Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...