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首页> 外文期刊>Journal of mass spectrometry: JMS >Enantiomeric differentiation of β-amino alcohols under electrospray ionization mass spectrometric conditions
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Enantiomeric differentiation of β-amino alcohols under electrospray ionization mass spectrometric conditions

机译：电喷雾电离质谱条件下β-氨基醇的对映异构

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摘要

The enantiomeric differentiation of a series of chiral β-amino alcohols (A) is attempted, for the first time, by applying the kinetic method using L-proline, L-tryptophan, 4-iodo-L-phenylalanine or 3, 5-diiodo-L-tyrosine as the chiral references (Ref) and Cu~(2+) or Ni~(2+) ion (M) as the central metal ion. The trimeric diastereomeric adduct ions, [M+(Ref)_2+A-H]~+, formed under electrospray ionization conditions, are subjected for collision-induced dissociation (CID) experiments. The products ions, formed by the loss of either a reference or an analyte, detected in the CID spectra are evaluated for the enantiomeric differentiation. All the references showed enantiomeric differentiation and the R_(chiral) values are better for the aromatic alcohols than for aliphatic alcohols. Notably, the R_(chiral) values of the aliphatic amino alcohols enhanced when Ni~(2+) is used as the central metal ion. The experimental results are well supported by computational studies carried out on the diastereomeric dimeric complexes. The computational data of amino alcohols is correlated with that of amino acids to understand the structural interaction of amino alcohols with reference molecule and central metal ion and their role on the stabilization of the dimeric complexes. Application of flow injection MS/MS method is also demonstrated for the enantiomeric differentiation of the amino alcohols.
机译：通过使用L-脯氨酸，L-色氨酸，4-碘-L-苯丙氨酸或3,5-二碘的动力学方法，首次尝试了一系列手性β-氨基醇（A）的对映异构体分化。 -L-酪氨酸作为手性参考（Ref），Cu〜（2+）或Ni〜（2+）离子（M）作为中心金属离子。在电喷雾电离条件下形成的三聚体非对映异构体加成离子[M +（Ref）_2 + A-H]〜+用于碰撞诱导解离（CID）实验。对在CID光谱中检测到的由于参比物或分析物的丢失而形成的产物离子，进行对映体差异评估。所有参考文献均显示对映体差异，并且芳族醇的R_（手性）值优于脂族醇。值得注意的是，当Ni〜（2+）用作中心金属离子时，脂族氨基醇的R_（手性）值提高。对非对映二聚体进行的计算研究充分支持了实验结果。氨基醇的计算数据与氨基酸相关，以了解氨基醇与参考分子和中心金属离子的结构相互作用及其在二聚配合物稳定中的作用。还证明了流动注射MS / MS方法在氨基醇对映异构体鉴别中的应用。

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