Chiral 1,5-disubstituted 1,2,3-triazoles-versatile tools for foldamers and peptidomimetic applications
Journal article, 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.

Author

Anna Said Stålsmeden

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry, Organic Chemistry

Andrew Paterson

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry

Imola Cs Szigyártó

Hungarian Academy of Sciences

Linda Thunberg

AstraZeneca AB

Johan Johansson

AstraZeneca AB

Tamas Beke-Somfai

Hungarian Academy of Sciences

Nina Kann

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry, Physical Chemistry

Organic and Biomolecular Chemistry

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

Vol. 18 10 1957-1967

Subject Categories

Polymer Chemistry

Polymer Technologies

Organic Chemistry

DOI

10.1039/d0ob00168f

More information

Latest update

3/31/2020