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Assessment and Application of Marfey's reagent and analogs in Enantioseparation: A decade's perspective.
Biomedical Chromatography ( IF 1.8 ) Pub Date : 2020-09-22 , DOI: 10.1002/bmc.4990
Sonika Sethi 1 , Jürgen Martens 2 , Ravi Bhushan 3
Affiliation  

Of the various methods available for high‐performance liquid chromatography separation of enantiomers (of e.g. amino acids and amino group containing compounds) by the pre‐column derivatization approach, use of Marfey’s reagent has been most successful with continued application since its introduction in 1984. The reagent is prepared from difluoro dinitro benzene by nucleophilic substitution of one of its F atoms by l‐alanine amide. There is flexibility to prepare several chiral variants (by substituting the F atom with different chiral auxiliaries) and to tailor the hydrophobicity and resolution, ultimately, of the diastereomeric derivatives. The present paper assesses and reviews applications of Marfey’s reagent and its chiral variants (i.e. other FDNP reagents) for enantioseparation of certain amino group containing drugs/amino acids, and to provide some case studies on enantiomeric separations that are important for the pharmaceutical industry. Various explanations for separation mechanism and elution order using FDNP reagents are included and the question of the configuration of the corresponding enantiomer using an indirect approach has also been addressed.

中文翻译:

Marfey试剂和类似物在对映分离中的评估和应用:十年的前景。

通过柱前衍生化方法进行高效液相色谱分离对映异构体(例如氨基酸和含氨基基团的化合物)的各种方法中,自1984年问世以来,Marfey试剂的使用一直是最成功的,并且一直在继续应用。所述试剂选自二氟二硝基苯通过它的F原子中的一个的亲核取代制备由1-丙氨酸酰胺。可以灵活地制备几种手性变体(通过将F原子替换为不同的手性助剂),并最终调整非对映异构体衍生物的疏水性和拆分度。本文评估和审查了Marfey试剂及其手性变异体(即其他FDNP试剂)在某些含氨基的药物/氨基酸的对映体分离中的应用,并提供了一些对制药业重要的对映体分离的案例研究。包括对使用FDNP试剂的分离机理和洗脱顺序的各种解释,并且还解决了使用间接方法对映体的构型问题。
更新日期:2020-09-22
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