基于荧光的高通量筛选胺和氨基酸衍生物的对映体过量,Chemistry - A European Journal

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基于荧光的高通量筛选胺和氨基酸衍生物的对映体过量
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2016-06-06 , DOI: 10.1002/chem.201601614
Elena G. Shcherbakova ₁ , Valentina Brega ₁ , Tsuyoshi Minami ₂ , Sara Sheykhi ₁ , Tony D. James ₃ , Pavel Anzenbacher ₁

Affiliation

报道了一种在水存在下对映体过量的胺衍生物的高精度和可靠的筛选方法。通过自组装手性二醇型染料（BINOL，VANOL和VAPOL），2-甲酰基苯基硼酸和形成亚氨基硼酸酯的手性胺，可以实现基于荧光的筛选系统。胺分析物的结构和手性决定了非对映异构亚氨基硼酸酯的稳定性，进而显示出差异荧光。荧光信号反映了手性胺的对映体纯度，并用于高通量阵列中。该阵列能够识别出对映体过量的胺，氨基酯和氨基醇。除定性分析外，还成功进行了定量实验。对添加剂（例如水或柠檬酸盐）的作用进行了研究，以深入了解亚氨基硼酸酯的稳定性。结果表明，上述添加剂使不稳定的酯不稳定，而稳定的酯保持不变。因此，水和柠檬酸盐的存在导致非对映体亚氨基硼酸酯之间的差异增加，并有助于手性胺的对映异构。

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Toward Fluorescence‐Based High‐Throughput Screening for Enantiomeric Excess in Amines and Amino Acid Derivatives

A highly accurate and reliable screening method for enantiomeric excess of amine derivatives in the presence of water is reported. The fluorescence‐based screening system has been realized by self‐assembly of chiral diol‐type dyes (BINOL, VANOL and VAPOL), 2‐formylphenylboronic acid, and chiral amines forming iminoboronate esters. The structure and chirality of the amine analytes determine the stability of the diastereomeric iminoboronate esters, which in turn display differential fluorescence. The fluorescence signal reflects the enantiomeric purity of the chiral amines and was utilized in high‐throughput arrays. The arrays were able to recognize enantiomeric excess of amines, amino esters, and amino alcohols. In addition to qualitative analysis, quantitative experiments were successfully performed. Studies of the role of additives such as water or citrate were carried out to gain insight into the stability of the iminoboronate esters. It is shown that the above additives destabilize less stable esters while the stable esters remain unchanged. Thus, the presence of water and citrate leads to increased difference between the diastereomeric iminoboronates and contributes to the enantiodiscrimination of the chiral amines.

更新日期：2016-06-06

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