Design of chiral monochloro-s-triazine reagents for the liquid chromatographic separation of amino acid enantiomers.
A series of chiral derivatizing reagents (CDRs) was synthesized by nucleophilic replacement of one chlorine atom in cyanuric chloride (2,4,6-trichloro-1,3,5-triazine; s-triazine) by alkoxy (methoxy, butoxy, 1,1,1-trifluoroethoxy) or aryloxy groups (phenoxy, nitrophenoxy, phenylphenoxy, 4-methylcoumaryloxy), and displacement of a second chlorine by L-alanine amide, L-phenylalanine amide, L-proline tert.-butyl ester, or Boc-L-lysine tert.-butyl ester. Further, CDRs were investigated in which two chlorine atoms in cyanuric chloride were substituted consecutively by L-valine amide and L-phenylalanine amide. The resulting CDRs having a remaining reactive chlorine were tested for their capability of derivatizing DL-amino acids followed by liquid chromatographic separation of the resulting diastereomers.
Brückner
H
H
Interdisciplinary Research Center, Department of Food Sciences, Institute of Nutritional Science, Justus-Liebig-University of Giessen, Heinrich-Buff-Ring 26, 35392 Giessen, Germany. hans.brueckner@ernaehrung.uni-giessen.de
Wachsmann
M
M
D000596:Amino Acids / Q000737:chemistry / Q000302:isolation & purification*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D007202:Indicators and Reagents / Q000737:chemistry*; D013237:Stereoisomerism; D014227:Triazines / Q000737:chemistry*
D000596:Amino Acids; D007202:Indicators and Reagents; D014227:Triazines