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为了开发具有高效手性识别能力的新型多糖类手性固定相,合成了5种糖单元2-位具有邻苯二甲酰亚胺,而3,6-位同时具有4种不同苯基氨基甲酸酯基团(2-氯、3-氯、4-氯和3,5二氯取代的苯基氨基甲酸酯)和一种无取代的苯基氨基甲酸酯基团的壳聚糖类衍生物,并将其涂覆在氨丙基硅胶表面制备成HPLC手性固定相.利用红外光谱和核磁氢谱对所合成的衍生物进行结构表征与分析,并应用HPLC法评价其对10种对映体的手性识别能力.研究结果表明:这些新型壳聚糖类手性固定相的手性识别能力受苯基氨基甲酸酯取代基中芳环上侧基的引入位置、数量和空间位阻的影响较大.同时色谱测试中所使用流动相的成分对该类手性固定相的识别能力也具有较大影响.进一步探讨了这些衍生物的氨基甲酸酯残基核磁氢谱中N—H质子的化学位移和红外光谱中N—H波数与手性识别能力之间的关系.
In order to develop a novel polysaccharide chiral stationary phase with high chiral recognition ability, five kinds of sugar units were synthesized with phthalimide at the 2-position and 4-phenylalanine at the 3,6-position Chitosans of the formate groups (2-chloro, 3-chloro, 4-chloro and 3,5dichloro-substituted phenylcarbamates) and an unsubstituted phenylcarbamate group Class derivatives were prepared and coated on the surface of aminopropyl silica gel to prepare HPLC chiral stationary phase.The structure and characterization of the synthesized derivatives were characterized by IR and 1H NMR and their The chiral recognition ability of these enantiomers was studied.The results show that the chiral recognition ability of these novel chitosan chiral stationary phases is affected by the introduction position, The steric hindrance has a great influence on the chiral stationary phase.At the same time, the composition of the mobile phase used in the chromatographic test also has a great influence on the recognition ability of these chiral stationary phases.Moreover, the urethane residue NMR spectra of these derivatives were also discussed Chemical shifts of N-H protons and the relationship between the N-H wavenumber and the chiral recognition ability in the infrared spectrum .