Separation and determination of the tryptophan enantiomers

  • Katalin Lóki
  • Péter Sára
  • Éva Vargáné Visi
  • Csilla Albert
  • Sz. Salamon
  • János Csapó
Kulcsszavak: racemization, tryptophan, mercaptoethanesulfonic acid, p-toluenesulfonic acid


Diastereoisomers of L- and D-tryptophan were formed with a chiral reagent 1-thio-β-D-glucose tetraacetate and o-phthaldialdehyde and they were separated from the derivatives of the other amino acids that occur in food proteins on an achiral column by high performance liquid chromatography. Mercaptoethanesulfonic acid that is an adequate agent for hydrolyzing proteins made the derivatization with o-phthaldialdehyde and 1-thio-β-D-glucose tetraacetate impossible, contrary the reaction completed in the presence of p-toluenesulfonic acid, but the oxidative losses during hydrolysis is significant. During boiling, the racemization of tryptophan can be detected above pH=9 after 12 hours, but the rate of conversion was lower than expected (<1%). The concentration decrease of L-tryptophan after 24 h was 2−5% depending on pH. Besides racemization other reactions e.g. oxidative deterioration may played a role in the loss of L- tryptophan.

Hogyan kell idézni
Lóki, K., Sára, P., Vargáné Visi, Éva, Albert, C., Salamon, S., & Csapó, J. (2006). Separation and determination of the tryptophan enantiomers. Acta Agraria Kaposváriensis, 10(2), 341-348. Elérés forrás
Poster Section

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