Homochiral membrane bilayers organize biological functions in all domains of life. The membrane’s permeability—its key property—correlates with a molecule’s lipophilicity, but the role of the membrane’s rich and uniform stereochemistry as a permeability determinant is largely ignored in empirical and computational measurements. Here, we describe a new approach to measuring permeation using continuously generated microfluidic droplet interface bilayers (DIBs, generated at a rate of 480 per minute) and benchmark this system by monitoring fluorescent dye DIB permeation over time. Enantioselective permeation of alkyne-labelled amino acids (Ala, Val, Phe, Pro) and dipeptides through a chiral phospholipid bilayer was demonstrated using DIB transport measurements; the biological l enantiomers permeated faster than the d enantiomers (from 1.2-fold to 6-fold for Ala to Pro). Enantioselective permeation both poses a potentially unanticipated criterion for drug design and offers a kinetic mechanism for the abiotic emergence of homochirality via chiral transfer between sugars, amino acids and lipids.

同手性膜双层在生命的所有领域组织生物学功能。膜的渗透性——其关键特性——与分子的亲脂性相关，但在经验和计算测量中，膜丰富且均匀的立体化学作为渗透性决定因素的作用在很大程度上被忽略了。在这里，我们描述了一种使用连续生成的微流体液滴界面双层（DIB，以每分钟 480 次的速度生成）测量渗透的新方法，并通过监测荧光染料 DIB 随时间的渗透来对该系统进行基准测试。使用 DIB 转运测量证明了炔烃标记的氨基酸（Ala、Val、Phe、Pro）和二肽通过手性磷脂双层的对映选择性渗透；生物l对映异构体比d对映异构体渗透得更快（从 Ala 到 Pro 的 1.2 倍到 6 倍）。对映选择性渗透既为药物设计提出了一个潜在的意想不到的标准，又为通过糖、氨基酸和脂质之间的手性转移来非生物出现同手性提供了动力学机制。