From glucose to enantiopure morpholino β-amino acid: a new tool for stabilizing γ-turns in peptides
Literature Information
Publication Date
2019-02-12
DOI
10.1039/C8QO01116H
Impact Factor
5.281
Authors
Raffaella Bucci, Alessandro Contini, Francesca Clerici, Sara Pellegrino, Maria Luisa Gelmi
View Original
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.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
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8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
![6,7-Dihydro-5H-pyrrolo[1,2-a]imidazole-6-carboxylic acid structure](https://static.chemtradehub.com/structs/136/1369160-12-2-6524.webp "6,7-Dihydro-5H-pyrrolo[1,2-a]imidazole-6-carboxylic acid structure")
6,7-Dihydro-5H-pyrrolo[1,2-a]imidazole-6-carboxylic acid
CAS Number:
1369160-12-2
Molecular Formula:
C7H8N2O2
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