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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
09:34

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Published on: February 6, 2020

Diels-Alder cycloadditions in water for the straightforward preparation of peptide-oligonucleotide conjugates

Vicente Marchán1, Samuel Ortega, Daniel Pulido

  • 1Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, Martí i Franquès 1-11, E-08028, Barcelona, Spain. vmarchan@ub.edu

Nucleic Acids Research
|February 16, 2006
PubMed

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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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In a Diels–Alder reaction, the diene is usually an electron-rich system and acts as a nucleophile, whereas the dienophile is electron-deficient and functions as an electrophile. Much like the diene, the nature of the dienophile significantly impacts the outcome of the reaction.
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