From glucose to enantiopure morpholino β-amino acid: a new tool for stabilizing γ-turns in peptides. Issue 7 (19th February 2019)

• Record Type: Journal Article
• Authors: Bucci, Raffaella; Contini, Alessandro; Clerici, Francesca; Pellegrino, Sara; Gelmi, Maria Luisa
• Is Part Of: Organic chemistry frontiers. Volume 6:Issue 7(2019)
• Page Start: 972
• Page End: 982
• Publication Date: 2019-02-19
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c8qo01116h
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : "Environmentally sustainable" synthesis of a new enantiopure morpholino β-amino acid from glucose: a new tool for exotic peptide architectures. 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.