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

Abstract

A new cyclic enantiopure β-amino acid, named β-Morph, containing the morpholino ring, was obtained in gram scale starting from 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 able to induce an inverse γ-turn in Leu-Val containing sequences. Key element for the γ-turn formation might be the oxygen atom of morpholino ring that could drive the spatial orientation of 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.

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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, Accepted Manuscript

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

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

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