Chiral 1,5-disubstituted 1,2,3-triazoles-versatile tools for foldamers and peptidomimetic applications
Artikel i vetenskaplig tidskrift, 2020

1,4- A nd 1,5-Disubstituted triazole amino acid monomers have gained increasing interest among peptidic foldamers, as they are easily prepared via Cu- A nd Ru-catalyzed click reactions, with the potential for side chain variation. While the latter is key to their applicability, the synthesis and structural properties of the chiral mono-or disubstituted triazole amino acids have only been partially addressed. We here present the synthesis of all eight possible chiral derivatives of a triazole monomer prepared via a ruthenium-catalyzed azide alkyne cycloaddition (RuAAC). To evaluate the conformational properties of the individual building units, a systematic quantum chemical study was performed on all monomers, indicating their capacity to form several low energy conformers. This feature may be used to effect structural diversity when the monomers are inserted into various peptide sequences. We envisage that these results will facilitate new applications for these artificial oligomeric compounds in diverse areas, ranging from pharmaceutics to biotechnology.

Författare

Anna Said Stålsmeden

Chalmers, Kemi och kemiteknik, Kemi och biokemi, Organisk kemi

Andrew Paterson

Chalmers, Kemi och kemiteknik, Kemi och biokemi

Imola Cs Szigyártó

Magyar Tudomanyos Akademia

Linda Thunberg

AstraZeneca AB

Johan Johansson

AstraZeneca AB

Tamas Beke-Somfai

Magyar Tudomanyos Akademia

Nina Kann

Chalmers, Kemi och kemiteknik, Kemi och biokemi, Fysikalisk kemi

Organic and Biomolecular Chemistry

1477-0520 (ISSN) 1477-0539 (eISSN)

Vol. 18 10 1957-1967

Ämneskategorier

Polymerkemi

Polymerteknologi

Organisk kemi

DOI

10.1039/d0ob00168f

Mer information

Senast uppdaterat

2020-03-31