Determination of the Absolute Configuration of 2-Hydroxyglutaric Acid, 5-Oxoproline and Vigabatrin in Urine by Chiral Derivatization and 13C or 19F NMR

• Autorzy: Bal D. , Gryff-Keller A.
• Konferencja: 1st Symp. on NMR in Chemistry, Biology and Medicine; 8-10 Semptember, Warsaw, Poland. Issue dedicated to honour Prof. Witanowski
• Języki publikacji: EN

Abstrakty

EN

Procedures for enantiomeric recognition of 2-hydroxyglutaric acid and 5-oxoproline - markers ofmetabolic diseases, and of vigabatrin - an antiepileptic drug, suitable for urine samples, have been elaborated. They rely upon derivatization of the metabolites with a chiral reagent; this is made without separation of these compounds from a biological sample. The diastereotopic metabolite derivatives are then distinguished using 13C or 19F NMR spectroscopy. This procedure is not so simple as one proposed previously, but, as opposite to the latter method, it seems to be unfailing and still not too complicated.

Słowa kluczowe

EN

NMR; absolute configuration; metabolic disease; vigabatrin

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2006
• Tom: Vol. 80, nr 7
• Strony: 1021--1030
• Opis fizyczny: Bibliogr. 27 poz., rys.

Twórcy

autor

Bal D.

autor

Gryff-Keller A.

• Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland

Bibliografia

• 1. Sewell A.C., Heil M., Podebrad F. and Mosandl A., Eur. J. Pediatr., 157, 185 (1998).
• 2. Heil M., Podebrad F., Beck T., Mosandl A., Sewell A.C. and Bohles H., J. Chromatogr. B, 714, 119 (1998).
• 3. Rashed M.S., Aboul-Enein H.Y., AlAmoudi M., Jakob M., Al-Ahaideb L.Y., Abbad A., Shabib S. and Al-Jishi E., Biomed. Chromatogr., 16, 191 (2002).
• 4. Duran M., Ketting D., Kamerling J.P., Gerwig G.J., Yliegenthart J.F.G. and Wadman S.K., J. Chro­matogr., 143, 117(1977).
• 5. Chalmers R.A., Lawson A.M., Watts R.W.E., Tavill A.S., Kamerling J.P., Hey E. and Ogilvie D., J. Inher. Metab. Dis., 3, 11 (1980).
• 6. Duran M., Kamerling J.P., Bakker H.D., van Gennip A.H. and Wadman S.K., J. Inher. Metab. Dis., 3, 109(1980).
• 7. Barth P.G., Hoffmann G.F., Jaeken J., Wanders R.J.A., Duran M., Jansen G.A., Jakobs C., Lehnert W., Hanefeld F., Valk J., Schutgens R.B.H., Trefz F.K., Hartung H.P., Chamoles N.A., Sfaello Z. and Caruso U., J. Inher. Metab. Dis., 16, 753 (1993).
• 8. Rashed M.S., AlAmoudi M. and Aboul-Enein H.Y., Biomed. Chromatogr., 14, 317 (2000).
• 9. Pitt J.J. and Hauser S., Clin. Chem., 44, 1497 (1998).
• 10. Gatti G., Bonomi L, Jannuzzi G. and Perucca E., Curr. Pharm. Design, 6, 839 (2000).
• 11. Tomson T.J., J. Neurol, 251, 1043 (2004).
• 12. Vauzelle-Kervroedan F., Rey E., Pons G., d'Athis P, Chiron C., Dulac O., Dumas C. and Olive G., Br. J. Clin. Pharmacol, 42, 779 (1996).
• 13. Vermeij T.A.C. and Edelbroek P.M., J. Chromatogr. B, 716, 233 (1998).
• 14. Vallat C., Rivier F., Bellet H., de Bomier B.M. and Mion H., Epilepsia, 37, 803 (1996).
• 15. Lahat E., Ben-Zeev B., Złotnik J. and Sela B.A., Pediatr. Neurol., 21, 460 (1999).
• 16. Podebrad F., Heil M., Beck T., Mosandl A., Sewell A.C. and Bohles H., Clin. Chim. Acta, 292,93 (2000).
• 17. Bal D., Gradowska W. and Gryff-Keller A., J. Pharm. Biomed. Anal, 28, 1061 (2002).
• 18. Winitz M., Bloch-Frankenthal L., Izumiya N., Birnbaum S.M., Baker C.G. and Greenstein J.P., J. Am. Chem. Soc., 78, 2423 (l956).
• 19. Saijo S., Wada M., Himizu J. and Ishida A., Chem. Pharm. Bull., 28, 1449 (1980).
• 20. Wei Z.Y. and Knaus E.E., Tetrahedron, 50, 5569 (1994).
• 21. Dale J.A., Duli D.L. and Mosher H.S., J. Org. Chem., 34, 2543 (1969).
• 22. Rothchild R., Enantiomer, 5, 457 (2000).
• 23. Wenzel T.J. and Wilcox J.D, Chirality, 15, 256 (2003).
• 24. Peters J.A., Huskens J. and Raber D.J., Prog. Nucl. Magn. Reson. Spectrosc., 28, 283 (1996) .
• 25. Seco J.M., Quinoa E. and Riguera R., Chem. Rev., 104, 17 (2004).
• 26. Sullivan G.R., Dale J.A. and Mosher H.S., J. Org. Chem., 38, 2143 (1973).
• 27. Tran A., O'Mahoney T., Rey E., Mai J., Mumford J.P. and Olive G., Br. J. Clin. Pharmacol, 45, 409 (1998).