Premium
Assessment and application of Marfey’s reagent and analogs in enantioseparation: a decade’s perspective
Author(s) -
Sethi Sonika,
Martens Jürgen,
Bhushan Ravi
Publication year - 2021
Publication title -
biomedical chromatography
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.4
H-Index - 65
eISSN - 1099-0801
pISSN - 0269-3879
DOI - 10.1002/bmc.4990
Subject(s) - chemistry , reagent , enantiomer , diastereomer , derivatization , nucleophile , amino acid , elution , chiral derivatizing agent , chromatography , combinatorial chemistry , amide , nucleophilic substitution , organic chemistry , high performance liquid chromatography , chiral column chromatography , catalysis , biochemistry
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.