Fyles Thomas M, Hu Chi-Wei, Luong Horace
Department of Chemistry, University of Victoria, Victoria, British Columbia, Canada, V8W 3P6.
J Org Chem. 2006 Oct 27;71(22):8545-51. doi: 10.1021/jo0615753.
A simple synthesis of oligoesters from TBDMS-protected-beta- and THP-protected-omega-hydroxycarboxylic acids using a solid-phase synthesis protocol is reported. Procedures were optimized for the efficient production of ion channel candidates in high purity with minimal purification. The product oligoesters were evaluated for ion transport activity using a fluorescent dye/vesicle assay. Oligoesters produced by this strategy show structure-dependent activity; the most active compounds are closely comparable to previously known oligoesters, but are available at a fraction of the synthetic effort.
报道了一种使用固相合成方案从叔丁基二甲基硅烷基（TBDMS）保护的β-羟基羧酸和四氢吡喃（THP）保护的ω-羟基羧酸简单合成低聚酯的方法。对程序进行了优化，以高效生产高纯度的离子通道候选物，且纯化步骤最少。使用荧光染料/囊泡测定法评估产物低聚酯的离子转运活性。通过该策略制备的低聚酯表现出结构依赖性活性；活性最高的化合物与先前已知的低聚酯相当，但合成工作量仅为其一小部分。
