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使用自组装八面体铁(II)-亚胺配合物测定手性胺对映体过量值

Chiral amine enantiomeric excess determination using self-assembled octahedral Fe(II)-imine complexes.

作者信息

Dragna Justin M, Gade Alexandra M, Tran Lee, Lynch Vince M, Anslyn Eric V

机构信息

Water Lens LLC, Houston, Texas.

出版信息

Chirality. 2015 Apr;27(4):294-8. doi: 10.1002/chir.22426. Epub 2015 Feb 9.

DOI:10.1002/chir.22426
PMID:25664936
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4394993/
Abstract

A receptor assembly composed of iron(II) triflate and pyridine-2,6-dicarbaldehyde was used to determine the enantiomeric excess (ee) of alpha-chiral primary amines using circular dichroism spectroscopy. The alpha chiral amines condense with the dialdehyde to form a diimine, which forms a 2:1 octahedral complex with iron(II). The ee values of unknown concentrations of alpha-chiral amines were determined by constructing calibration curves for each amine and then measuring the ellipticity at 600 nm. This improves our previously reported assay for ee determination of chiral primary amines by further increasing the wavelength at which CD is measured and reducing the absolute error of the assay.

摘要

由三氟甲磺酸铁(II)和2,6-吡啶二甲醛组成的受体组件用于通过圆二色光谱法测定α-手性伯胺的对映体过量(ee)。α-手性胺与二醛缩合形成二亚胺,该二亚胺与铁(II)形成2:1的八面体配合物。通过为每种胺构建校准曲线,然后在600nm处测量椭圆率,确定未知浓度的α-手性胺的ee值。通过进一步提高测量圆二色性的波长并降低测定的绝对误差,这改进了我们先前报道的用于手性伯胺ee测定的方法。

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本文引用的文献

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J Am Chem Soc. 2013 Dec 4;135(48):18052-5. doi: 10.1021/ja410428b. Epub 2013 Nov 21.
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Chirality sensing using stereodynamic probes with distinct electronic circular dichroism output.使用具有不同电子圆二色性输出的立体动态探针进行手性感应。
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An exciton-coupled circular dichroism protocol for the determination of identity, chirality, and enantiomeric excess of chiral secondary alcohols.
一种用于确定手性仲醇的手性、对映体过量和对映体纯度的激子耦合圆二色性协议。
J Am Chem Soc. 2012 Apr 25;134(16):7117-25. doi: 10.1021/ja301252h. Epub 2012 Apr 11.
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J Am Chem Soc. 2012 Mar 7;134(9):4398-407. doi: 10.1021/ja211768v. Epub 2012 Feb 22.
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A simple method for the determination of enantiomeric excess and identity of chiral carboxylic acids.一种手性羧酸对映体过量和对映体纯测定的简单方法。
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Rapid determination of enantiomeric excess of α-chiral cyclohexanones using circular dichroism spectroscopy.使用圆二色光谱法快速测定 α-手性环己酮的对映体过量。
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