Related Experiment Video
Updated: May 28, 2026

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
Published on: February 6, 2020
Amino acid derivatives of perylenediimide and their N-H···O peptide bond dipoles-templated solid state assembly into
Cyprien Lemouchi1, Sergey Simonov, Leokadiya Zorina
1Laboratoire MOLTECH-Anjou, CNRS, University of Angers, 49045, Angers, France.
Abstract:
A methodology is proposed to provide direct access in good yields to peptide residues-appended perylenediimides PDI-(Cl(4))-[Gly-Ala(OEt)](2), 2a, PDI-(Cl(4))-[Gly-Val(OEt)](2), 2b and PDI-(Cl(4))-[Gly-Gly(OEt)](2), 2c from a generic perylenediimide (PDI) platform symmetrically functionalized with carboxylic acids at the imide sites, PDI-(Cl(4))-[Gly(OH)](2), 1. The latter is obtained in good purity by a non classical two-steps route avoiding the many, notoriously cumbersome successive chromatography steps typical of PDI chemistry, and including a single final purification allowing to crystallize the water soluble pure diacid 1, of great interest in its own right for further developments in a variety of fields. Then, the synthesis, crystallization and analysis of the crystal structures of 2a and 2b reveal a common pattern of self-assembly of the outer peptide residues based on collections of parallel N-H···O peptidic hydrogen bonds running alongside stacks where the constraints imposed upon on the inner PDI skeletons by long range interaction of these parallel electric dipoles reduce the dihedral angles around the bay regions by as much as 11% down to 32°.
Related Concept Videos
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
Structure of Amines
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
Aldehydes and Ketones with Amines: Imine Formation Mechanism
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
Structures of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...

