Lefevre Sara, Héloin Alexandre, Pitrat Delphine, Mulatier Jean-Christophe, Vanthuyne Nicolas, Jean Marion, Dutasta Jean-Pierre, Guy Laure, Martinez Alexandre
Laboratoire de Chimie, École Normale Supérieure de Lyon , CNRS, UCBL 46, Allée d'Italie, F-69364 Lyon, France.
Aix Marseille Université , Centrale Marseille, CNRS, iSm2 UMR 7313, 13397 Marseille, France.
J Org Chem. 2016 Apr 15;81(8):3199-205. doi: 10.1021/acs.joc.6b00159. Epub 2016 Apr 4.
New host compounds combining a cyclotriveratrylene (CTV) unit and three binaphthol moieties have been synthesized enantiomerically and diastereomerically pure. The use of a chemical correlation allows for the assignment of their absolute configuration. The energy barrier of epimerization was measured, suggesting that no intramolecular hydrogen bonding occurs between the hydroxyl groups of the binaphthols. These open-shell host compounds were then tested in the recognition of carbohydrates; a preferential binding of mannose toward glucose was observed, and good diastereoselectivities were reached (up to 1:10). This recognition of sugar derivatives by open-shell CTV-based host compounds is unprecedented and opens up the way for a wider use of this easily accessible class of molecules as chiral sensors.
已合成出对映体纯和非对映体纯的新型主体化合物，其结合了一个环三藜芦烃（CTV）单元和三个联萘酚部分。通过化学关联可确定它们的绝对构型。测量了差向异构化的能垒，表明联萘酚的羟基之间未发生分子内氢键作用。然后对这些开壳主体化合物进行了碳水化合物识别测试；观察到甘露糖对葡萄糖有优先结合，并且达到了良好的非对映选择性（高达1:10）。这种基于开壳CTV的主体化合物对糖衍生物的识别是前所未有的，为更广泛地将这类易于获取的分子用作手性传感器开辟了道路。
