Use of chiral monohalo-s-triazine reagents for the liquid chromatographic resolution of dl-amino acids
Use of chiral monohalo-s-triazine reagents for the liquid chromatographic resolution of dl-amino acids
复制标题
手性单卤代-s-三嗪试剂用于 dl-氨基酸的液相色谱拆分
DOI：
10.1016/0021-9673(92)87190-j
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发表时间：
1992
影响因子：
4.1
通讯作者：
B. Strecker
中科院分区：
文献类型：
--
作者：
H. Brückner;B. Strecker
通过与甲醇、2-萘酚、1-甲氧基萘或4-氨基偶氮苯反应，亲核取代三卤-s-三嗪（2,4,6-三卤-1,3,5-三嗪）、氰尿酰氯或氰尿酰氟中的一个卤素原子（氯、氟） 紫外线吸收、发色的二卤代-s-三嗪。通过与1-丙氨酸酰胺反应进一步取代这些化合物中的卤素原子，得到手性单卤代-s-三嗪。剩余的卤素原子通过与选定的对映氨基酸反应而被取代，形成非对映异构体衍生物，其通过反相(C18)高效液相色谱法使用水、乙腈和三氟乙酸的混合物作为洗脱液进行分离。由于其可以在与各种手性部分组合的大量检测基团中进行选择，因此该方法被认为是设计和构建适用于柱前衍生化和氨基酸对映体间接液相色谱分离的定制试剂的通用方法。
Nucleophilic replacement of one halogen atom (chlorine, fluorine) in the trihalo-s-triazines (2,4,6-trihalo-1,3,5-triazines), cyanuric chloride or cyanuric fluoride by reaction with either methanol, 2-naphthol, 1-methoxynaphthalene, or 4-aminoazobenzene furnished ultraviolet-absorbing, fluorescent of chromogenic dihalo-s-triazines. Substitution of a further halogen atom in these compounds by reaction withl-alanine amide provided chiral monohalo-s-triazines. The remaining halogen atom was substituted by reaction with selectedd- orl-amino acids to form diastereomeric derivatives which were separated by reverse-phase (C18) high-performance liquid chromatography by using mixtures of water, acetonitrile and trifluoroacetic acid as eluents. Because of its possibilities for selection among a large number of detection groups in combination with various chiral moieties, the approach is considered to be a general method for the design and construction of tailor-made reagents suitable for precolumn derivatization and indirect liquid chromatographic separation of amino acid enantiomers.