Skip to main content

Chiral Mobile-Phase Additives in HPLC Enantioseparations

  • Protocol
Chiral Separations

Part of the book series: Methods in Molecular Biology ((MIMB,volume 1985))

Abstract

High-performance liquid chromatography (HPLC) is one of the main separation techniques for chiral drugs. Among the chiral HPLC techniques available, the chiral mobile-phase additive (CMPA) technique is a valuable method for the direct enantioseparation of chiral chemical entities. In the CMPA method, the chiral selector is dissolved in the mobile phase while the stationary phase is achiral. Interaction with the analyte enantiomers results in the formation of transient diastereomeric complexes. These complexes differ in their formation constants and/or distribution between the (achiral) stationary phase and the mobile phase resulting in an enantioseparation. This chapter describes the HPLC separation applying CMPA methods by several most useful types of chiral selectors including chiral ligand exchangers, macrocyclic antibiotics, and cyclodextrins.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Protocol
USD 49.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Inai Y, Ousaka N, Miwa Y (2006) Theoretical comparison between three-point and two point binding modes for chiral discrimination up on the N-terminal sequence of 310-helix. J Polym 38:432–441

    Article  CAS  Google Scholar 

  2. Davankov VA (1997) The nature of chiral recognition: is it a three-point interaction? Chirality 9:99–102

    Article  CAS  Google Scholar 

  3. León AG, Olives AI, Martin MA, del Castello B (2007) The role of β-cyclodextrin and hydroxypropyl-β-cyclodextrin in the secondary chemical equilibria associated to the separation of β-carbolines by HPLC. J Incl Phenom Macrocycl Chem 57:577–583

    Article  Google Scholar 

  4. Davankov VA (1997) Analytical chiral separation methods. Pure Appl Chem 69:1469–1474

    Article  CAS  Google Scholar 

  5. Armstrong DW, Tang Y, Chen S et al (1994) Macrocyclic antibiotics as a new class of chiral selectors for liquid chromatography. Anal Chem 66:1473–1484

    Article  CAS  Google Scholar 

  6. Bressolle F, Audran M, Pham TN, Vallon JJ (1996) Cyclodextrins and enantiomeric separations of drugs by liquid chromatography and capillary electrophoresis: basic principles and new developments. J Chromatogr B Biomed Sci Appl 687:303–336

    Article  Google Scholar 

  7. Zeng S, Zong J, Pan L, Wang S (1996) Separation of ofloxacin enantiomers by using preparative chiral chromatography. Chin J Chromatogr 14:280–281

    CAS  Google Scholar 

  8. Hu X, Guo X, Sun S et al (2017) Enantioseparation of nine indanone and tetralone derivatives by HPLC using carboxymethyl-β-cyclodextrin as the mobile phase additive. Chirality 29:38–47

    Article  CAS  Google Scholar 

  9. Bhushan R, Agarwal C (2010) Resolution of beta blocker enantiomers by TLC with vancomycin as impregnating agent or as chiral mobile phase additive. J Planar Chromatogr 23:7–13

    Article  CAS  Google Scholar 

  10. Natalini B, Giacche N, Sardella R et al (2010) Computational studies for the elucidation of the enantiomer elution order of amino acids in chiral ligand-exchange chromatography. J Chromatogr A 1217:7523–7527

    Article  CAS  Google Scholar 

  11. Berthod A, Yu T, Kullman JP et al (2000) Evaluation of the macrocyclic glycopeptide A-40,926 as a high-performance liquid chromatographic chiral selector and comparison with teicoplanin chiral stationary phase. J Chromatogr A 897:113–129

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Su Zeng .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2019 Springer Science+Business Media, LLC, part of Springer Nature

About this protocol

Cite this protocol

Yu, L., Wang, S., Zeng, S. (2019). Chiral Mobile-Phase Additives in HPLC Enantioseparations. In: Scriba, G.K.E. (eds) Chiral Separations. Methods in Molecular Biology, vol 1985. Humana, New York, NY. https://doi.org/10.1007/978-1-4939-9438-0_5

Download citation

  • DOI: https://doi.org/10.1007/978-1-4939-9438-0_5

  • Publisher Name: Humana, New York, NY

  • Print ISBN: 978-1-4939-9437-3

  • Online ISBN: 978-1-4939-9438-0

  • eBook Packages: Springer Protocols

Publish with us

Policies and ethics