1. 01/11/96*1 Ergot alkaloids as novel chiral selectors in CE Benno A. Ingelse, Jetse C. Reijenga, Henk A. Claessens, Frans M. Everaerts and Mirko Flieger Eindhoven University of Technology, The Netherlands Academy of Sciences of the Czech Republic

2. Ergot alkaloids General formula 1-allyl-terguride

3. Experimental: v P/ACE 2200 Beckman Instruments v Capillary: 50 µm, 300/370 mm, PVA-coated  BGE:  -alanine/acetate + allyl-terguride, pH 4.0, I=50 mM v UV-detection, 200 nm v Samples: 10 -4 M

4. Experimental setup

5. Typical electropherogram using ergot skeletons as chiral selector Abs. [AU] time [minutes]

6. Influence of pH on the resolution of some racemic organic acids Abs. [AU] time [minutes]

7. Influence of terguride concentration on the mobility of the analytes 0510152025 concentration allyl-terguride [mM] 12 14 16 18 20 22 mpa1 mpa2 vm1 vm2 m(eff)

8. Determination of the K c -value of vanilmandelic acid enantiomers 0510152025 concentration allyl-terguride (mM) 1.00 1.10 1.20 1.30 1.40 K c µ 1 /µ A

9. Influence of MeOH on the chiral separation of the racemic organic acids Abs. [AU] time [minutes]

10. Influence of terguride concentration on the mobility of the analytes in 50% MeOH 010203040506070 concentration allyl-terguride [mM] 8 10 12 14 16 mpa1 mpa2 vm1 vm2 m(eff)

11. Determination of the K c -value of  -methyl- phenylacetic acid enantiomers using MeOH 0510152025 concentration allyl-terguride (mM) 1.00 1.10 1.20 1.30 1.40 K c µ 1 /µ A

12. Full separation of some racemic organic acids using 25 mg/mL allyl-terguride Abs. [AU] time [minutes]

13. Selectivity with and without MeOH 0 204060 Concentration allyl-terguride [mM] 0.00 0.02 0.04 0.06 mandelic acid 50% MeOH0% MeOH S 0204060 Concentration allyl-terguride [mM] 0.00 0.02 0.04 0.06 tropic acid 50% MeOH0% MeOH S

14. Conclusions v Allyl-terguride has great potential as a chiral selector for organic acids v The dissociated acid forms stereoselective complexes with the ergot alkaloid v Solubility of the ergot-alkaloid in water is limited v Methanol increases solubility v Methanol influences stereoselectivity