Related Experiment Video
Updated: Jun 3, 2026

Synthesis and Structure Determination of µ-Conotoxin PIIIA Isomers with Different Disulfide Connectivities
Published on: October 2, 2018
Copper-Mediated Trimerization of Diazopeptides Generates Peptide Derivatives of Cis- and Trans-Aconitic Acid That
Timothy P Curran1, Lilly L Pubillones1, Alessandro Marrone2
1Department of Chemistry, Trinity College, 300 Summit Street, Hartford, Connecticut 06106, United States.
Abstract:
The reaction of two diazopeptides with CuI in MeCN produces peptide derivatives of [E] and [Z]-aconitic acid via a trimerization reaction. Best yields of the trimeric products occur when 0.5 equiv of CuI is used. The conformations of the peptide derivatives of [E] and [Z]-aconitic acid were probed using computational and NMR methods. Both the isomers adopt a conformation having two intramolecular hydrogen bonds, where two of the peptide chains are parallel to each other, while the other is perpendicular.
Related Concept Videos
Protein Folding
Protein Structure Is Critical to Its Biological Function
Proteins perform a wide range of biological functions such as catalyzing chemical reactions, providing...
Preparation of Amides
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...
Peptide Bonds
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Disubstituted Cyclohexanes: cis-trans Isomerism
In cyclohexane, the substituents can occupy different positions generating distinct isomers.

