Bhushan Ravi, Kumar Rajender
Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee 247 667, India.
Biomed Chromatogr. 2010 Jan;24(1):66-82. doi: 10.1002/bmc.1355.
Penicillamine (PenA) is a nonproteinogenic amino acid containing a thiol group. The three functional groups in penicillamine undergo characteristic chemical reactions and differ in their ability to participate in various chemical and biochemical reactions. d-penicillamine is more active pharmacologically, while the l-isomer occurs 'naturally'. This review deals with the enantioresolution of PenA both by direct and indirect methods using liquid chromatography. HPLC separation of its diastereomers prepared with different chiral derivatizing reagents (on reversed-phase columns) and separation of the derivatives prepared with achiral reagents (on chiral columns or via ligand exchange mode) has been discussed. Separation of enantiomers tagged with achiral reagent (to add a chromophore for ehanced detection) when there is no diastereomer formation has been considered separately. In addition, application of PenA and its derivatives as chiral selector for enentioresolution of certain other compounds has also been discussed.
青霉胺（PenA）是一种含有巯基的非蛋白质氨基酸。青霉胺中的三个官能团会发生特征性化学反应，并且它们参与各种化学和生化反应的能力有所不同。d-青霉胺在药理上更具活性，而l-异构体“天然”存在。本综述涉及使用液相色谱通过直接和间接方法对青霉胺进行对映体拆分。讨论了用不同手性衍生试剂制备的其非对映异构体的高效液相色谱分离（在反相柱上）以及用非手性试剂制备的衍生物的分离（在手性柱上或通过配体交换模式）。当不形成非对映异构体时，对用非手性试剂标记的对映体（添加发色团以增强检测）的分离已单独考虑。此外，还讨论了青霉胺及其衍生物作为某些其他化合物对映体拆分的手性选择剂的应用。
