一种新型手性吡咯烷官能团修饰的β-环糊精合成与构象研究

Synthesis and Conformation of a Novelβ-cyclodextrin Modified with Chiral Pyrrolidine Functional Group

以N-Boc-L-脯氨酸为原料,制备了一种新型的手性吡咯烷官能团修饰的β-环糊精.最终产物经1 HNMR、13CNMR、ESI-HRMS表征确认了结构.经过二维核磁谱对产物构象进行研究,发现手性侧链可以进入环糊精的空腔中.量化计算(PM6)研究表明,侧链进入空腔形成的自我包结的构象为能量最低构象,与实验结论一致.

With L-proline as start material, a novel β-cyclodextrin modified with chiral pyrrolidine func tional group was prepared. The structure was confirmed by IH NMR,13C NMR,ESI-HRMS. The configuration of the modified β-cyclodextrin was studied via 2D NMR and the result of ROESY showed the chiral pyrrolidine group could enter the cavity of the β-cyclodextrin. The results of quantum calculation （PM6） showed the lowest energy conformation is the self-inclusion conformation.