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Circularly Polarized Luminescence of Aluminum Complexes for Chiral Sensing of Amino Acid and Amino Alcohol.
Chemistry - An Asian Journal ( IF 3.5 ) Pub Date : 2019-12-27 , DOI: 10.1002/asia.201901480
Qingxian Jin 1 , Fulin Wang 1, 2 , Shuyu Chen 1 , Liming Zhou 1 , Hejin Jiang 2 , Li Zhang 2 , Minghua Liu 2
Affiliation  

Determination of the absolute configuration (AC) of chiral molecules is a key issue in many fields related to chirality such as drug development, the asymmetric reaction screening, and the structure determination of natural compounds. Although various methods, such as X-ray crystallography and NMR spectroscopy, are used to determine the AC, a simple and cheap alternative method is always anticipated. So far, electronic circular dichroism (ECD) spectroscopy has been widely used to ascertain the AC and enantiomeric excess (ee) values by applying appropriate organic probes. Here, circularly polarized luminescence (CPL) spectroscopy was applied to determine the AC and ee values of a series of amino acid and amino alcohol. The measurements were conducted by mixing the amino acids or amino alcohols with an achiral 1-hydroxy-2-naphthaldehyde. Upon in situ formation of the Schiff base complexes, the system showed emission enhancement and CPL in the presence of Al3+ , whose intensity and sign can be used to assign the chiral sense of the amino acids and amino alcohols. The authenticity of the method was further compared with the established CD spectroscopy, revealing that CPL spectra of formed Al3+ complex were effective to determine the AC of chiral species.

中文翻译:

铝配合物的圆偏振发光,用于氨基酸和氨基醇的手性传感。

在许多与手性有关的领域中,例如药物开发,不对称反应筛选以及天然化合物的结构确定,手性分子的绝对构型(AC)的确定是一个关键问题。尽管使用各种方法(例如X射线晶体学和NMR光谱法)来确定AC,但始终期望有一种简单且便宜的替代方法。到目前为止,通过应用适当的有机探针,电子圆二色性(ECD)光谱已被广泛用于确定AC和对映体过量(ee)值。在这里,圆偏振发光(CPL)光谱用于确定一系列氨基酸和氨基醇的AC和ee值。通过将氨基酸或氨基醇与非手性1-羟基-2-萘醛混合来进行测量。在原位形成Schiff碱配合物后,系统在Al3 +存在下显示出发射增强和CPL,其强度和符号可用于指定氨基酸和氨基醇的手性。该方法的真实性进一步与已建立的CD光谱进行了比较,表明所形成的Al3 +配合物的CPL光谱对于确定手性物种的AC是有效的。
更新日期:2019-12-27
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