Liu Zhiwei, Remsing Richard C, Liu Dahui, Moyna Guillermo, Pophristic Vojislava
Department of Chemistry & Biochemistry and Center for Drug Design and Delivery, University of the Sciences in Philadelphia, 600 South 43rd Street, Philadelphia, Pennsylvania 19104-4495, USA.
J Phys Chem B. 2009 May 21;113(20):7041-4. doi: 10.1021/jp902155j.
We combine molecular modeling and NMR methods to better understand intramolecular hydrogen bonding (H-bonding) in a frequently used arylamide foldamer building block, ortho-methoxy-N-methylbenzamide. Our results show that solvents have a profound influence on the cumulative number and stabilizing effects of intramolecular H-bonds, and thus conformational preferences, of foldamers based on this compound. While intramolecular H-bonds are conserved in aprotic environments, they are significantly disrupted in protic solvents. Furthermore, these solvent effects can be accurately quantified using the computational approach presented here. The results could have significant implications in foldamer design, particularly for applications in aqueous environments.
我们结合分子建模和核磁共振方法，以更好地理解常用的芳基酰胺折叠体构建单元邻甲氧基-N-甲基苯甲酰胺中的分子内氢键。我们的结果表明，溶剂对基于该化合物的折叠体的分子内氢键的累积数量和稳定作用以及构象偏好有深远影响。虽然分子内氢键在非质子环境中得以保留，但在质子溶剂中会被显著破坏。此外，使用本文提出的计算方法可以准确量化这些溶剂效应。这些结果可能对折叠体设计有重大影响，特别是在水性环境中的应用。
