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Modular solid-phase synthesis of electrophilic cysteine-selective ethynyl-phosphonamidate peptides

Sarah Hansen1,2, Jan Vincent V Arafiles1, Philipp Ochtrop1,2

  • 1Leibniz-Forschungsinstitut für Molekulare Pharmakologie (FMP), Chemical Biology Department, Robert-Rössle-Str. 10, 13125 Berlin, Germany. hackenbe@fmp-berlin.de.

Chemical Communications (Cambridge, England)
|July 6, 2022
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Preparation of Amides01:29

Preparation of Amides

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...