2‐Pyridone Formation: An Efficient Method for the Solid‐Phase Synthesis of Homodimers

This study presents an efficient method for on‐resin dimer generation through self‐condensation of 3,3‐dimethoxypropionic acid‐modified molecules, resulting in 2‐pyridones. The approach demonstrated remarkable versatility by producing homodimers of peptides, peptoids, and non‐peptidic ligands. Its e...

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Bibliographic Details
Published in:Chemistry : a European journal 2024-01, Vol.30 (2), p.e202302937-n/a
Main Authors: Abboud, Skander A., Kodadek, Thomas
Format: Article
Language:English
Subjects:
Chemistry
Condensation resins
Homodimer
Ligands
peptide
Peptides
Pyridone
Solid phase methods
Solid phase synthesis
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Summary:This study presents an efficient method for on‐resin dimer generation through self‐condensation of 3,3‐dimethoxypropionic acid‐modified molecules, resulting in 2‐pyridones. The approach demonstrated remarkable versatility by producing homodimers of peptides, peptoids, and non‐peptidic ligands. Its ease of application, broad utility, and mild reaction conditions not only hold significance for peptide and peptoid research but also offer potential for the on‐resin development of a wide range of bivalent ligands. A highly efficient and operationally simple method is presented for the solid‐phase synthesis of homodimeric protein ligands from a single precursor through acid‐ or I2/acetone‐mediated formation of a 2‐pyridone linkage.
ISSN:0947-6539
1521-3765
1521-3765
DOI:10.1002/chem.202302937