Brückner H, Wachsmann M
Interdisciplinary Research Center, Department of Food Sciences, Institute of Nutritional Science, Justus-Liebig-University of Giessen, Heinrich-Buff-Ring 26, 35392 Giessen, Germany.
J Chromatogr A. 2003 May 23;998(1-2):73-82. doi: 10.1016/s0021-9673(03)00638-1.
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.
通过用烷氧基（甲氧基、丁氧基、1,1,1-三氟乙氧基）或芳氧基（苯氧基、硝基苯氧基、苯基苯氧基、4-甲基香豆素氧基）亲核取代三聚氯氰（2,4,6-三氯-1,3,5-三嗪；均三嗪）中的一个氯原子，并用L-丙氨酸酰胺、L-苯丙氨酸酰胺、L-脯氨酸叔丁酯或Boc-L-赖氨酸叔丁酯取代第二个氯原子，合成了一系列手性衍生试剂（CDR）。此外，还研究了其中三聚氯氰中的两个氯原子被L-缬氨酸酰胺和L-苯丙氨酸酰胺连续取代的CDR。对所得具有剩余活性氯的CDR进行了衍生化DL-氨基酸的能力测试，然后对所得非对映异构体进行液相色谱分离。
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