Diffusion-Enhanced Amide Bond Formation on a Solid Support

Johnny N. Naoum, Israel Alshanski, Agata Gitlin-Domagalska, Moshe Bentolila, Chaim Gilon, Mattan Hurevich*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

Mixing of polystyrene resins in solid-phase synthesis is performed by shaking or gentle agitation of the reaction vessel to avoid breaking the brittle beads. These mixing strategies result in poor diffusion to and into the beads. Using a large excess of reagents is the common way to compensate for these deficiencies. We use fast overhead stirring for performing coupling reactions on a solid support. We show that fast overhead stirring enhances the efficiency of amide bond formation on the solid support compared to the state-of-the-art mixing method, while preserving the integrity of the beads. We find that fast overhead stirring minimizes the effect of decomposition of the activated species by increasing the diffusion-dependent coupling reaction. This allows decreasing the excess of reagents used for the multistep synthesis of peptides, thus providing a greener and more sustainable alternative for peptide synthesis on solid supports.

Original languageAmerican English
Pages (from-to)2733-2739
Number of pages7
JournalOrganic Process Research and Development
Volume23
Issue number12
DOIs
StatePublished - 20 Dec 2019

Bibliographical note

Publisher Copyright:
Copyright © 2019 American Chemical Society.

Keywords

  • amide bond formation
  • diffusion
  • peptides
  • solid-phase synthesis
  • sustainable chemistry

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