Jump to main content
Jump to site search

Issue 7, 2019
Previous Article Next Article

From glucose to enantiopure morpholino β-amino acid: a new tool for stabilizing γ-turns in peptides

Author affiliations

Abstract

A new cyclic enantiopure β-amino acid, named β-Morph, containing the morpholino ring, was obtained in gram scale starting from an α-D-glucopyranose enantiopure material, focusing on the “environmental sustainability” concept. A series of ultrashort model peptides containing β-Morph were prepared. β-Morph was found to be able to induce an inverse γ-turn in Leu-Val containing sequences. The key element for the γ-turn formation might be the oxygen atom of the morpholino ring that could drive the spatial orientation of the NH of amino acid i + 1, through an unusual hydrogen bond. This datum was confirmed by QTAIM calculations. Interestingly, when two β-Morph-Leu-Val repeats are present in the peptide, two γ-turns can be formed, as supported by NMR experiments and aMD and H-REMD calculations.

Graphical abstract: From glucose to enantiopure morpholino β-amino acid: a new tool for stabilizing γ-turns in peptides

Back to tab navigation

Supplementary files

Publication details

The article was received on 16 Oct 2018, accepted on 11 Feb 2019 and first published on 12 Feb 2019


Article type: Research Article
DOI: 10.1039/C8QO01116H
Citation: Org. Chem. Front., 2019,6, 972-982

  •   Request permissions

    From glucose to enantiopure morpholino β-amino acid: a new tool for stabilizing γ-turns in peptides

    R. Bucci, A. Contini, F. Clerici, S. Pellegrino and M. L. Gelmi, Org. Chem. Front., 2019, 6, 972
    DOI: 10.1039/C8QO01116H

Search articles by author

Spotlight

Advertisements