Lee Sanghoo, Choi Youngjin, Lee Sangsan, Jeong Karpjoo, Jung Seunho
Department of Microbial Engineering, and Bio/Molecular Informatics Center, Konkuk University, 1 Hwaynag-dong Gwangjin-gu, Seoul 143-701, South Korea.
Chirality. 2004 Mar;16(3):204-10. doi: 10.1002/chir.20010.
Cyclosophoraoses isolated from Rhizobium meliloti, as an NMR chiral shift agent, were used to discriminate propranolol enantiomers. Continuous variation plot made from the complex of cyclosophoraoses with propranolol showed that the diastereomeric complex had predominantly 1:1 stoichiometry through UV spectroscopic analysis. The chiral recognition of propranolol enantiomers by cyclosophoraoses was investigated through the determination of binding constant based on the (13)C NMR chemical shift changes. The averaged K(obs) values from the plots were 55.7 M(-1) for (R)-(+)-propranolol and 36.6 M(-1) for (S)-(-)-propranolol, respectively. Enantioselectivity (alpha = K(R+)/K(S(-)) of 1.52 was then obtained. Computational calculation also revealed that (R)-(+) propranolol was more tightly bound with cyclosophoraose than (S)-(-)-propranolol due to the enhanced van der Waals interaction.
从苜蓿根瘤菌中分离出的环索藻糖作为核磁共振手性位移试剂，用于区分普萘洛尔对映体。通过紫外光谱分析，由环索藻糖与普萘洛尔形成的配合物绘制的连续变化图表明，非对映体配合物的化学计量比主要为1:1。通过基于(13)C核磁共振化学位移变化测定结合常数，研究了环索藻糖对普萘洛尔对映体的手性识别。图中(R)-(+)-普萘洛尔的平均K(obs)值为55.7 M(-1)，(S)-(-)-普萘洛尔的平均K(obs)值为36.6 M(-1)。然后获得了1.52的对映选择性(α = K(R+)/K(S(-)))。计算计算还表明，由于范德华相互作用增强，(R)-(+)-普萘洛尔比(S)-(-)-普萘洛尔与环索藻糖的结合更紧密。
