Reflections on a Copenhagen–Minneapolis Axis in Bioorganic Chemistry

George Barany, Paul R. Hansen

Research output: Contribution to journalArticlepeer-review

Abstract

The international peptide community rejoiced when one of its most distinguished members, Morten Meldal of Denmark, shared the 2022 Nobel Prize in Chemistry. In fact, the regiospecific solid-phase “copper(I)-catalyzed 1,3-dipolar cycloaddition of terminal alkynes to azides” (CuACC) reaction—that formed the specific basis for Meldal’s recognition—was reported first at the 17th American Peptide Symposium held in San Diego in June 2001. The present perspective outlines intertwining conceptual and experimental threads pursued concurrently in Copenhagen and Minneapolis, sometimes by the same individuals, that provided context for Meldal’s breakthrough discovery. Major topics covered include orthogonality in chemistry; the dithiasuccinoyl (Dts) protecting group for amino groups in α-amino acids, carbohydrates, and monomers for peptide nucleic acids (PNA); and poly(ethylene glycol) (PEG)-based solid supports such as PEG–PS, PEGA, and CLEAR [and variations inspired by them] for solid-phase peptide synthesis (SPPS), solid-phase organic synthesis (SPOS), and combinatorial chemistry that can support biological assays in aqueous media.

Original languageEnglish (US)
Article number1317
JournalMolecules
Volume29
Issue number6
DOIs
StatePublished - Mar 2024

Bibliographical note

Publisher Copyright:
© 2024 by the authors.

Keywords

  • dithiasuccinoyl (Dts) protection of amines
  • glycopeptide synthesis
  • orthogonality in chemistry
  • poly(ethylene glycol) (PEG)-based supports
  • solid-phase peptide synthesis (SPPS)

PubMed: MeSH publication types

  • Journal Article

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