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使用带有葡萄糖胺支链的模型非环双酰胺修饰对溶剂和受体结构对手性识别的影响。

The Impact of Solvent and the Receptor Structure on Chiral Recognition Using Model Acyclic Bisamides Decorated with Glucosamine Pendant Arms.

机构信息

Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.

出版信息

J Org Chem. 2020 Sep 18;85(18):11902-11907. doi: 10.1021/acs.joc.0c01693. Epub 2020 Aug 28.

DOI:10.1021/acs.joc.0c01693
PMID:32812751
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7506935/
Abstract

We investigated the influence of various factors (including solvent mixtures) on chiral recognition of chiral carboxylates, using the titration method under H NMR control. We found that strong binding carboxylates (geometrical matching) is not enough for the satisfactory differentiation of enantiomers. Moreover, solvent mixture studies indicate a significant influence of environment on the formation of diastereomeric complexes and variations among them. Our findings offer insights into the complementarity of chiral recognition processes.

摘要

我们使用核磁共振控制滴定法，研究了各种因素（包括溶剂混合物）对手性羧酸的手性识别的影响。我们发现，对于对映体的满意区分，强结合的羧酸（几何匹配）是不够的。此外，溶剂混合物研究表明，环境对非对映体配合物的形成及其变化有显著影响。我们的发现提供了对手性识别过程互补性的深入了解。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55e2/7506935/d62c04932433/jo0c01693_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55e2/7506935/f9d476307c8c/jo0c01693_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55e2/7506935/70d2604abaad/jo0c01693_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55e2/7506935/38eaba53752c/jo0c01693_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55e2/7506935/aba038b38a31/jo0c01693_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55e2/7506935/dc1e57f2d7cb/jo0c01693_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55e2/7506935/d62c04932433/jo0c01693_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55e2/7506935/f9d476307c8c/jo0c01693_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55e2/7506935/70d2604abaad/jo0c01693_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55e2/7506935/38eaba53752c/jo0c01693_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55e2/7506935/aba038b38a31/jo0c01693_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55e2/7506935/dc1e57f2d7cb/jo0c01693_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55e2/7506935/d62c04932433/jo0c01693_0006.jpg

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Molecules. 2020 Jan 18;25(2):401. doi: 10.3390/molecules25020401.
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Self-Assembly and Molecular Recognition in Water: Tubular Stacking and Guest-Templated Discrete Assembly of Water-Soluble, Shape-Persistent Macrocycles.
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