Luppi Gianluigi, Galeazzi Roberta, Garavelli Marco, Formaggio Fernando, Tomasini Claudia
Department of Chemistry "G. Ciamician", Alma Mater Studiorum, University of Bologna, 40126 Bologna, Italy.
Org Biomol Chem. 2004 Aug 7;2(15):2181-7. doi: 10.1039/B405856A. Epub 2004 Jul 14.
A total synthesis in solution and a conformational analysis of the homo-oligomers of (4R)-(2-oxo-1,3-oxazolidin-4-yl)-acetic acid (D-Oxac) to the tetramer level are described. As the D-Oxac building block contains both an oxazolidin-2-one and a beta-amino acid group, it may represent a new type of conformationally constrained tool for the construction of beta-pseudopeptide foldamers. A conformational investigation using NMR and an extensive, unconstrained analysis with a Monte Carlo search to the octamer level, both in water and in chloroform, showed that these homo-oligomers tend to fold in a regular helical structure in a competitive solvent, such as water. Since aqueous solutions are of major relevance for biological systems, these molecules are good candidates for application to these environments.
描述了(4R)-(2-氧代-1,3-恶唑烷-4-基)乙酸（D-恶唑烷酮）同聚物在溶液中的全合成以及至四聚体水平的构象分析。由于D-恶唑烷酮结构单元同时含有恶唑烷-2-酮和β-氨基酸基团，它可能代表一种用于构建β-假肽折叠体的新型构象受限工具。在水和氯仿中，使用核磁共振进行的构象研究以及通过蒙特卡罗搜索对八聚体水平进行的广泛、无约束分析表明，这些同聚物在竞争溶剂（如水）中倾向于折叠成规则的螺旋结构。由于水溶液与生物系统密切相关，这些分子是应用于这些环境的良好候选物。
