Rapid synthesis of cyclopropane-dipeptide analogues

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Development of a Backbone Cyclic Peptide Library as Potential Antiparasitic Therapeutics Using Microwave Irradiation
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Development of a Backbone Cyclic Peptide Library as Potential Antiparasitic Therapeutics Using Microwave Irradiation

Published on: January 26, 2016

Andrew McMath1, Dominique Guillaume

  • 1Laboratoire de Chimie Thérapeutique, Amiens, France.

Natural Product Research
|August 4, 2005
PubMed

Abstract:

The synthesis of cyclopropane-substituted nitrile-dipeptides is reported. The straightforward transformation of the nitrile function into an amide or methylketone function leads to dipeptide analogues of potentially interesting pharmacologic profile.

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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...

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