Gagnon Christina, Godin Éric, Minozzi Clémentine, Sosoe Johann, Pochet Corentin, Collins Shawn K
Département de Chimie, Centre for Green Chemistry and Catalysis, Université de Montréal, CP 6128 Station Downtown, Montréal, Québec H3C 3J7, Canada.
Science. 2020 Feb 21;367(6480):917-921. doi: 10.1126/science.aaz7381.
Macrocycles can restrict the rotation of substituents through steric repulsions, locking in conformations that provide or enhance the activities of pharmaceuticals, agrochemicals, aroma chemicals, and materials. In many cases, the arrangement of substituents in the macrocycle imparts an element of planar chirality. The difficulty in predicting when planar chirality will arise, as well as the limited number of synthetic methods to impart selectivity, have led to planar chirality being regarded as an irritant. We report a strategy for enantio- and atroposelective biocatalytic synthesis of planar chiral macrocycles. The macrocycles can be formed with high enantioselectivity from simple building blocks and are decorated with functionality that allows one to further modify the macrocycles with diverse structural features.
大环化合物可通过空间排斥作用限制取代基的旋转，锁定构象，从而赋予或增强药物、农用化学品、香料化学品及材料的活性。在许多情况下，大环化合物中取代基的排列赋予了平面手性元素。由于难以预测平面手性何时会出现，以及赋予选择性的合成方法数量有限，平面手性一直被视为一个棘手的问题。我们报道了一种对映选择性和阻转选择性生物催化合成平面手性大环化合物的策略。这些大环化合物可由简单的构建单元以高对映选择性形成，并带有官能团，使人们能够用各种结构特征进一步修饰大环化合物。
