Skip to main content
SpringerLink
Log in

Quantitative Analysis and Separation of Chiral (S)-Ethyl 3-Hydroxyglutarate in Bioconversion Mixtures by LC and TLC

  • Full Short Communication
  • Published:
Chromatographia Aims and scope Submit manuscript

Abstract

A convenient ion-pair LC procedure was firstly established for rapid analysis of ethyl 3-hydroxyglutarate (3-EHG) in an enzymatic-hydrolysis mixture, and the detection limit was as low as 0.45 μmol L−1; high repeatability was achieved with intra-day (n = 5) and inter-day (n = 5) relative standard deviation (RSD) values of 1.56 and 2.38%, respectively. The good linearity was established for 3-EHG concentration in the broad range from 0.005 to 0.30 mol L−1, with a coefficient (r) of 0.9992. (S)- and (R)-3-EHG were separated by normal-phase LC after simple derivatization with (R)-(+)-phenylethanamine, ee value (≥95%) of 3-EHG prepared by Lipase B catalyzed hydrolysis of diethyl 3-hydroxyglutatate (3-DHG) was determined after optimization of the mobile phase, and the RSD was 0.75% (n = 9) for repeatability. The results showed that the above methods were highly reproducible and reliable for analysis and separation of (S)-3-EHG from bioconversion mixture.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3

References

  1. Kathawala FG (1991) Med Res Rev 11:121–146. doi:10.1002/med.2610110201

    CAS  Google Scholar 

  2. Tobert JA (2003) Nat Rev Drug Discov 2:517–526

    Article  CAS  Google Scholar 

  3. Müller M (2005) Angew Chem Int Edit 44:362–365. doi:10.1002/anie.200460852

    Article  Google Scholar 

  4. Tempkin G, Abel S, Chen CP, Underwood R, Prasad K, Chen KM, Repic O, Blacklock TJ (1997) Tetrahedron 53:10659–10670. doi:10.1016/S0040-4020(97)00686-8

    Article  CAS  Google Scholar 

  5. Ohrlein R, Baisch G (2003) Adv Synth Catal 345:713–715. doi:10.1002/adsc.200303028

    Article  Google Scholar 

  6. Jacobsen EE, Hoff BH, Moen AR, Anthonsen T (2003) J Mol Catal B Enzym 21:55–58. doi:10.1016/S1381-1177(02)00138-8

    Article  CAS  Google Scholar 

  7. Gopalan AS, Sih CJ (1984) Tetrahedron Lett 25:5235–5238. doi:10.1016/S0040-4039(01)81572-0

    Article  CAS  Google Scholar 

  8. Rosen T, Watanabe M, Heathcock CH (1984) J Org Chem 49:3657–3659. doi:10.1021/jo00193a044

    Article  CAS  Google Scholar 

  9. Pursch M, Sander LC, Egelhaaf HJ, Raitza M, Wise SA, Oelkrug D, Albert K (1999) J Am Chem Soc 121:3201–3213. doi:10.1021/ja983046p

    Article  CAS  Google Scholar 

  10. Sander LC, Sharpless KE, Craft NE, Wise SA (1994) Anal Chem 66:1667–1674. doi:10.1021/ac00082a012

    Article  CAS  Google Scholar 

  11. Okamoto M, Nobuhara K, Masatani M, Jinno K (1992) Chromatographia 33:203–207. doi:10.1007/BF02276183

    Article  CAS  Google Scholar 

  12. Bartha A, Vigh G, Varga-Puchony Z (1990) J Chromatogr A 499:423–434. doi:10.1016/S0021-9673(00)96989-9

    Article  CAS  Google Scholar 

  13. Dolan JW (1996) LC GC N Am 14:768

    CAS  Google Scholar 

  14. Snyder LR, Kirkland JJ, Glajch JL (1997) Practical HPLC method development, 2nd ed. Wiley, New York

    Google Scholar 

  15. Carson MC (2000) J Chromatogr A 885:343–350. doi:10.1016/S0021-9673(00)00471-4

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the Major Basic Research Development Program of China (973 Project, No. 2009CB724704).

Author information

Authors and Affiliations

  1. Institute of Bioengineering, Zhejiang University of Technology, Hangzhou, 310014, People’s Republic of China

    Hua-Ping Dong & Yu-Guo Zheng

Authors
  1. Hua-Ping Dong
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yu-Guo Zheng
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yu-Guo Zheng.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Dong, HP., Zheng, YG. Quantitative Analysis and Separation of Chiral (S)-Ethyl 3-Hydroxyglutarate in Bioconversion Mixtures by LC and TLC. Chroma 71, 85–89 (2010). https://doi.org/10.1365/s10337-009-1401-8

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1365/s10337-009-1401-8

Keywords

Search

Navigation