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呋喃糖环构象的鉴定及其形成的驱动因素。

Identification of the furanose ring conformations and the factors driving their adoption.

作者信息

Walczak Dominik, Sikorski Artur, Grzywacz Daria, Nowacki Andrzej, Liberek Beata

机构信息

Faculty of Chemistry, University of Gdańsk, Wita Stwosza 63, 80-308, Gdańsk, Poland.

Faculty of Chemistry, University of Gdańsk, Wita Stwosza 63, 80-308, Gdańsk, Poland.

出版信息

Carbohydr Res. 2023 Apr;526:108780. doi: 10.1016/j.carres.2023.108780. Epub 2023 Mar 3.

DOI:10.1016/j.carres.2023.108780
PMID:36944302
Abstract

Three groups of furanoses with restricted freedom of rotation on the C3-C4, C2-C3, and C1-C2 bonds, respectively, are presented. Conformational analysis of these furanoses is conducted based on the proton nuclear magnetic resonance (H NMR) spectroscopy, density functional theory (DFT) calculations, and X-ray analysis. It is shown that the particular group of the presented furanoses is locked in the specific conformation. These are the T-like, the E-like, and the T-like conformation, respectively. Characteristic H NMR spectra of these three conformations are presented and the factors influencing the conformational preferences of the analyzed furanoses are discussed.

摘要

分别展示了三组在C3-C4、C2-C3和C1-C2键上旋转自由度受限的呋喃糖。基于质子核磁共振(H NMR)光谱、密度泛函理论(DFT)计算和X射线分析对这些呋喃糖进行了构象分析。结果表明,所展示的特定组呋喃糖被锁定在特定构象中。它们分别是T型、E型和T型构象。给出了这三种构象的特征H NMR光谱,并讨论了影响所分析呋喃糖构象偏好的因素。

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