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一种不寻常的茚三酮基反应在 D,L-青霉胺间接手性拆分中的应用。

Application of an unusual ninhydrin-based reaction for the indirect chiral resolution of D,L-penicillamine.

机构信息

Department of Biomedical Sciences, Chair of Clinical Biochemistry, University of Sassari, Viale San Pietro 43/B, I-07100 Sassari, Italy.

出版信息

Talanta. 2011 Sep 30;85(4):1783-5. doi: 10.1016/j.talanta.2011.07.007. Epub 2011 Jul 12.

DOI:10.1016/j.talanta.2011.07.007
PMID:21872019
Abstract

An unusual reaction involving ninhydrin and aminothiols was exploited to set an indirect method for the chiral recognition of stereoisomers of penicillamine. Separation of diastereoisomers was achieved on a C18 column in isocratic mode by using a mixture of propionic acid (pH 3.0)/acetonitrile/water (10:10:80, v/v/v) as a mobile phase. Diastereoisomers were detected by a fluorescence detector in fairly short times (about 7 min) and with a good resolution. The lowest detectable amount of toxic isomer of penicillamine (l-enantiomer) in samples of the d-enantiomer, was around 0.01%. The method was also suitable for the indirect chiral recognition of other aminothiols such as cysteine and cysteinylglycine.

摘要

利用涉及水合茚三酮和氨基硫醇的特殊反应,建立了一种间接方法用于对青霉胺对映异构体进行手性识别。通过使用丙酸(pH 3.0)/乙腈/水(10:10:80,v/v/v)混合物作为流动相,在 C18 柱上以等度模式实现了非对映异构体的分离。通过荧光检测器在相当短的时间(约 7 分钟)内以良好的分辨率检测到非对映异构体。在 d-对映异构体样品中,最低可检测到的青霉胺(l-对映异构体)毒性异构体的量约为 0.01%。该方法也适用于其他氨基硫醇如半胱氨酸和半胱氨酰甘氨酸的间接手性识别。

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1
Application of an unusual ninhydrin-based reaction for the indirect chiral resolution of D,L-penicillamine.一种不寻常的茚三酮基反应在 D,L-青霉胺间接手性拆分中的应用。
Talanta. 2011 Sep 30;85(4):1783-5. doi: 10.1016/j.talanta.2011.07.007. Epub 2011 Jul 12.
2
Enantiomeric reversed-phase high-performance liquid chromatography resolution of D-/L-penicillamine after spirocyclization with ninhydrin and by using copper(II)-L-proline complex as a chiral selector in the mobile phase.茚三酮螺环化后,以铜(II)-L-脯氨酸络合物作为流动相中的手性选择剂,采用对映体反相高效液相色谱法拆分D-/L-青霉胺。
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