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

文献信息

发布日期 2019-02-12

DOI 10.1039/C8QO01116H

影响因子 5.281

作者

Raffaella Bucci, Alessandro Contini, Francesca Clerici, Sara Pellegrino, Maria Luisa Gelmi

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摘要

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.

期刊推荐

Journal of Organometallic Chemistry

Organic Preparations and Procedures International

European Journal of Wood and Wood Products

Russian Chemical Reviews

Proceedings of the National Academy of Sciences of the United States of America

Fibre Chemistry

Kinetics and Catalysis

Nature

Planta Medica

Helvetica Chimica Acta

来源期刊

Organic Chemistry Frontiers

CiteScore: 7.8

自引率: 8.7%

年发文量: 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

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

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